ANTIBIOTIC CC 1065 supplier | CasNO.69866-21-3

Name
Rachelmycin
EINECS
CAS No. 69866-21-3
Article Data5
CAS DataBase
Density 1.75g/cm³
Solubility
Melting Point
Formula C37H33 N7 O8
Boiling Point 704.36°C (rough estimate)
Molecular Weight 703.711
Flash Point
Transport Information
Appearance
Safety Deadly poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[(4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]benzo[1,2-b:4,3-b']dipyrrol-2(1H)-yl)carbonyl]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-,(7bR)-; Benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide,7-[[1,6-dihydro-4-hydroxy-5-methoxy-7-[(4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa[c]pyrrolo[3,2-e]indol-2(1H)-yl)carbonyl]benzo[1,2-b:4,3-b']dipyrrol-3(2H)-yl]carbonyl]-1,6-dihydro-4-hydroxy-5-methoxy-,(7bR,8aS)- (9CI); Cyclopropa[c]benzo[1,2-b:4,3-b']dipyrrole,benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxamide deriv.; (+)-CC 1065; Antibiotic CC1065; CC 1065; CC 1065, (+)-; MCMC 10279; NSC 298223; Rachelmycin
PSA 210.31000
LogP 4.62030

Synthetic route

: 112764-71-3
C37H34ClN7O8

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;	45%
With triethylamine In water; acetonitrile at 22℃; for 0.5h;	43%
With triethylamine In water; acetonitrile at 23℃; for 0.5h; Yield given;
With triethylamine In water; acetonitrile for 1h; Ambient temperature; Yield given;

: 110314-51-7
tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 3M HCl / ethyl acetate / 1 h / Ambient temperature 2: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 3: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 3 steps 1: 3N HCl / ethyl acetate / 0.75 h / 23 °C 2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen chloride gas / ethyl acetate / 0.67 h 2: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 3: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: 112836-67-6
(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 3: 3M HCl / ethyl acetate / 1 h / Ambient temperature 4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 2: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 3: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 4: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 5: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 2: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 3: 3N HCl / ethyl acetate / 0.75 h / 23 °C 4: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 5: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 6 steps 1: pyridine / 6 h / Ambient temperature 2: lithium chloride / dimethylformamide / 0.42 h / 80 °C 3: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 4: hydrogen chloride gas / ethyl acetate / 0.67 h 5: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 6: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: 110314-50-6
(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 2: 3M HCl / ethyl acetate / 1 h / Ambient temperature 3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 2: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 3: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 4: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 4 steps 1: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 2: 3N HCl / ethyl acetate / 0.75 h / 23 °C 3: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 4: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 4 steps 1: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 2: hydrogen chloride gas / ethyl acetate / 0.67 h 3: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 4: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: 110314-54-0
(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 2: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 2 steps 1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 2 steps 1: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 2: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: (3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 96 percent / methanol / 0 deg C - r.t., overnight 2: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C 3: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 4: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 5: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 6: 3M HCl / ethyl acetate / 1 h / Ambient temperature 7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 8: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 96 percent / methanol / 0 deg C - r.t., overnight
2: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
3: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
4: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
5: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
6: 3M HCl / ethyl acetate / 1 h / Ambient temperature
7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
8: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme

: 176685-39-5
(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 2: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 3: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 4: 3M HCl / ethyl acetate / 1 h / Ambient temperature 5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 6: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
2: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
3: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
4: 3M HCl / ethyl acetate / 1 h / Ambient temperature
5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
6: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme

: 176685-38-4
(S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C 2: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 3: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 4: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 5: 3M HCl / ethyl acetate / 1 h / Ambient temperature 6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 7: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C
2: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating
3: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature
4: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C
5: 3M HCl / ethyl acetate / 1 h / Ambient temperature
6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature
7: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature
View Scheme

: 38880-89-6
N-(2-hydroxy-4-nitrophenyl)benzamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 18 steps 1: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating 2: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 3: pyridine / tetrahydrofuran / 18 h / 22 °C 4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 5: CH2Cl2 / 10 h / 23 °C 6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 13: tetrahydrofuran / 20 h / 23 °C 14: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 15: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 16: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 17: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 18: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 18 steps
1: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating
2: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
3: pyridine / tetrahydrofuran / 18 h / 22 °C
4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
5: CH2Cl2 / 10 h / 23 °C
6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
13: tetrahydrofuran / 20 h / 23 °C
14: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
15: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
16: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
17: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
18: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: 112764-62-2
N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 2.) 10percent aq. HCl / 1.) CH2Cl2, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h 2: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C 3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 4: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 5: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 6: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 7: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 8: tetrahydrofuran / 3 h / 23 °C 9: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 10: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 11: 3N HCl / ethyl acetate / 0.75 h / 23 °C 12: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 13: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 2.) 10percent aq. HCl / 1.) CH2Cl2, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h
2: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C
3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
4: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
5: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
6: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
7: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
8: tetrahydrofuran / 3 h / 23 °C
9: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
10: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
11: 3N HCl / ethyl acetate / 0.75 h / 23 °C
12: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
13: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112764-63-3
5-amino-1-benzoyl-7-(benzyloxy)-3-methyl-N5-(phenylsulfonyl)indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 7: tetrahydrofuran / 20 h / 23 °C 8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 12: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 12 steps 1: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C 2: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 3: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 4: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 5: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 6: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 7: tetrahydrofuran / 3 h / 23 °C 8: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 9: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 10: 3N HCl / ethyl acetate / 0.75 h / 23 °C 11: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 12: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 12 steps
1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
7: tetrahydrofuran / 20 h / 23 °C
8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
12: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 12 steps
1: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C
2: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
3: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
4: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
5: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
6: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
7: tetrahydrofuran / 3 h / 23 °C
8: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
9: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
10: 3N HCl / ethyl acetate / 0.75 h / 23 °C
11: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
12: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 98296-23-2
6-(6-Carbamoyl-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carbonyl)-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 2 steps 1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

: 112764-73-5
N-(4-Amino-2-benzyloxy-phenyl)-benzamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 16 steps 1: pyridine / tetrahydrofuran / 18 h / 22 °C 2: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 3: CH2Cl2 / 10 h / 23 °C 4: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 5: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 6: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 7: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 8: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 9: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 10: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 11: tetrahydrofuran / 20 h / 23 °C 12: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 13: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 14: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 15: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 16: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 16 steps
1: pyridine / tetrahydrofuran / 18 h / 22 °C
2: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
3: CH2Cl2 / 10 h / 23 °C
4: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
5: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
6: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
7: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
8: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
9: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
10: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
11: tetrahydrofuran / 20 h / 23 °C
12: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
13: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
14: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
15: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
16: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: 112764-72-4
N-(2-Benzyloxy-4-nitro-phenyl)-benzamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 17 steps 1: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 2: pyridine / tetrahydrofuran / 18 h / 22 °C 3: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 4: CH2Cl2 / 10 h / 23 °C 5: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 6: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 7: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 8: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 9: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 10: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 11: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 12: tetrahydrofuran / 20 h / 23 °C 13: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 14: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 15: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 16: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 17: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 17 steps
1: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
2: pyridine / tetrahydrofuran / 18 h / 22 °C
3: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
4: CH2Cl2 / 10 h / 23 °C
5: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
6: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
7: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
8: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
9: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
10: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
11: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
12: tetrahydrofuran / 20 h / 23 °C
13: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
14: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
15: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
16: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
17: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: N-<4-(benzoylimino)-3-(benzyloxy)-2,5-cyclohexadien-1-ylidene>benzenesulfonamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1: CH2Cl2 / 10 h / 23 °C 2: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 3: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 4: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 5: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 6: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 7: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 8: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 9: tetrahydrofuran / 20 h / 23 °C 10: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 11: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 12: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 13: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 14: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 14 steps
1: CH2Cl2 / 10 h / 23 °C
2: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
3: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
4: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
5: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
6: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
7: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
8: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
9: tetrahydrofuran / 20 h / 23 °C
10: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
11: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
12: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
13: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
14: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: 112764-74-6
N-(4-Benzenesulfonylamino-2-benzyloxy-phenyl)-benzamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 2: CH2Cl2 / 10 h / 23 °C 3: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 4: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 5: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 6: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 7: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 8: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 10: tetrahydrofuran / 20 h / 23 °C 11: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 12: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 13: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 14: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 15: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 15 steps
1: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
2: CH2Cl2 / 10 h / 23 °C
3: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
4: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
5: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
6: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
7: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
8: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
10: tetrahydrofuran / 20 h / 23 °C
11: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
12: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
13: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
14: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
15: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: N-(1-Benzoyl-7-benzyloxy-3-methyl-2-piperidin-1-yl-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 2: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 3: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 4: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 5: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 6: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 7: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 8: tetrahydrofuran / 20 h / 23 °C 9: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 10: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 11: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 12: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 13: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 13 steps
1: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
2: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
3: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
4: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
5: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
6: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
7: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
8: tetrahydrofuran / 20 h / 23 °C
9: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
10: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
11: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
12: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
13: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: 107890-45-9
PDE I dimer methyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / sodium dithionite, lithium hydroxide / tetrahydrofuran; methanol; H2O / 10 h / 45 °C 2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 3 steps 1: 84 percent / LiOH, Na2S2O4, water / tetrahydrofuran; methanol / 10 h / 45 °C 2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

: 112243-83-1
5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrahydrofuran / 20 h / 23 °C 2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 6: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 6 steps 1: tetrahydrofuran / 3 h / 23 °C 2: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 3: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 4: 3N HCl / ethyl acetate / 0.75 h / 23 °C 5: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 6: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: tetrahydrofuran / 20 h / 23 °C
2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
6: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 6 steps
1: tetrahydrofuran / 3 h / 23 °C
2: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
3: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
4: 3N HCl / ethyl acetate / 0.75 h / 23 °C
5: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
6: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112764-67-7
(1RS)-3-(Benzenesulfonyl)-5-(benzyloxy)-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 2: tetrahydrofuran / 20 h / 23 °C 3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 7: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 7 steps 1: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 2: tetrahydrofuran / 3 h / 23 °C 3: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 4: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 5: 3N HCl / ethyl acetate / 0.75 h / 23 °C 6: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 7: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
2: tetrahydrofuran / 20 h / 23 °C
3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
7: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 7 steps
1: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
2: tetrahydrofuran / 3 h / 23 °C
3: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
4: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
5: 3N HCl / ethyl acetate / 0.75 h / 23 °C
6: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
7: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112764-64-4
5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 20 h / 23 °C 7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 11 steps 1: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 2: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 3: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 4: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 3 h / 23 °C 7: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 8: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 9: 3N HCl / ethyl acetate / 0.75 h / 23 °C 10: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 11: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 11 steps
1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
6: tetrahydrofuran / 20 h / 23 °C
7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 11 steps
1: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h
2: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
3: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
4: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
5: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
6: tetrahydrofuran / 3 h / 23 °C
7: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
8: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
9: 3N HCl / ethyl acetate / 0.75 h / 23 °C
10: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
11: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112793-55-2
6-benzoyl-5-(benzyloxy)-1,2-dihydro-8-methyl-1-methylidene-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 4: tetrahydrofuran / 20 h / 23 °C 5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 9: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 9 steps 1: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 2: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 3: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 4: tetrahydrofuran / 3 h / 23 °C 5: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 6: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 7: 3N HCl / ethyl acetate / 0.75 h / 23 °C 8: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 9: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
4: tetrahydrofuran / 20 h / 23 °C
5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
9: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 9 steps
1: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
2: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
3: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
4: tetrahydrofuran / 3 h / 23 °C
5: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
6: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
7: 3N HCl / ethyl acetate / 0.75 h / 23 °C
8: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
9: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112764-66-6
6-benzoyl-5-(benzyloxy)-1,2-dihydro-1-(hydroxymethyl)-8-methyl-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 3: tetrahydrofuran / 20 h / 23 °C 4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 8: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 8 steps 1: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 2: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 3: tetrahydrofuran / 3 h / 23 °C 4: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 5: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 6: 3N HCl / ethyl acetate / 0.75 h / 23 °C 7: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 8: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 8 steps
1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
3: tetrahydrofuran / 20 h / 23 °C
4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
8: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 8 steps
1: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
2: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
3: tetrahydrofuran / 3 h / 23 °C
4: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
5: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
6: 3N HCl / ethyl acetate / 0.75 h / 23 °C
7: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
8: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 112764-65-5
1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 2: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 3: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 5: tetrahydrofuran / 20 h / 23 °C 6: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 7: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 8: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 9: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 10: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 10 steps 1: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 2: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 3: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 4: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 5: tetrahydrofuran / 3 h / 23 °C 6: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 7: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 8: 3N HCl / ethyl acetate / 0.75 h / 23 °C 9: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 10: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

Yield

Multi-step reaction with 10 steps
1: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
2: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
3: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
5: tetrahydrofuran / 20 h / 23 °C
6: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
7: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
8: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
9: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
10: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

Multi-step reaction with 10 steps
1: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C
2: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min
3: 83 percent / 5percent HCl / methanol / 2 h / 50 °C
4: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C
5: tetrahydrofuran / 3 h / 23 °C
6: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C
7: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C
8: 3N HCl / ethyl acetate / 0.75 h / 23 °C
9: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C
10: Et3N / H2O; acetonitrile / 0.5 h / 23 °C
View Scheme

: 121-88-0
2-Amino-5-nitrophenol

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 19 steps 1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C 2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating 3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 4: pyridine / tetrahydrofuran / 18 h / 22 °C 5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 6: CH2Cl2 / 10 h / 23 °C 7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 9: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 10: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 11: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 12: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 13: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 14: tetrahydrofuran / 20 h / 23 °C 15: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 16: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 17: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 18: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 19: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

Yield

Multi-step reaction with 19 steps
1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C
2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating
3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating
4: pyridine / tetrahydrofuran / 18 h / 22 °C
5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C
6: CH2Cl2 / 10 h / 23 °C
7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C
8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C
9: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h
10: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating
11: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min
12: 83 percent / acetyl chloride / methanol / 2 h / 50 °C
13: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C
14: tetrahydrofuran / 20 h / 23 °C
15: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C
16: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C
17: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C
18: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C
19: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C
View Scheme

: 108833-14-3
((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran / 90 h 2: pyridine / 6 h / Ambient temperature 3: lithium chloride / dimethylformamide / 0.42 h / 80 °C 4: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 5: hydrogen chloride gas / ethyl acetate / 0.67 h 6: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 7: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: triethylamine / tetrahydrofuran / 90 h
2: pyridine / 6 h / Ambient temperature
3: lithium chloride / dimethylformamide / 0.42 h / 80 °C
4: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
5: hydrogen chloride gas / ethyl acetate / 0.67 h
6: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
7: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme

: 101222-79-1
((S)-5-Benzyloxy-3-methanesulfonyl-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 3.4 M REDAL / tetrahydrofuran; toluene / 0.5 h / 85 °C 2: triethylamine / tetrahydrofuran / 90 h 3: pyridine / 6 h / Ambient temperature 4: lithium chloride / dimethylformamide / 0.42 h / 80 °C 5: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 6: hydrogen chloride gas / ethyl acetate / 0.67 h 7: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 8: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 3.4 M REDAL / tetrahydrofuran; toluene / 0.5 h / 85 °C
2: triethylamine / tetrahydrofuran / 90 h
3: pyridine / 6 h / Ambient temperature
4: lithium chloride / dimethylformamide / 0.42 h / 80 °C
5: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature
6: hydrogen chloride gas / ethyl acetate / 0.67 h
7: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature
8: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme

: 110314-49-3
(S)-5-Benzyloxy-1-methanesulfonyloxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carboxylic acid tert-butyl ester

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium chloride / dimethylformamide / 0.42 h / 80 °C 2: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 3: hydrogen chloride gas / ethyl acetate / 0.67 h 4: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 5: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

: C18H15ClN2O5S

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: dichloromethane; dimethyl sulfoxide / 29 h / 0 °C 2.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C 2.2: 2.5 h / -78 °C 3.1: dmap / acetonitrile / 1 h / 20 °C 4.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C 5.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C 6.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C 7.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C 8.1: boron trichloride / dichloromethane / 0.67 h / 0 °C 9.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr 10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C 12.2: 1 h / 20 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C 13.2: 4.17 h / 0 - 20 °C 14.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C 15.1: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 15 steps
1.1: dichloromethane; dimethyl sulfoxide / 29 h / 0 °C
2.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C
2.2: 2.5 h / -78 °C
3.1: dmap / acetonitrile / 1 h / 20 °C
4.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C
5.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C
6.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C
7.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C
8.1: boron trichloride / dichloromethane / 0.67 h / 0 °C
9.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr
10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C
12.2: 1 h / 20 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C
13.2: 4.17 h / 0 - 20 °C
14.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C
15.1: triethylamine / tetrahydrofuran / 1 h / 20 °C
View Scheme

: C13H11N3O2

: 69866-21-3
CC-1065

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: dmap / acetonitrile / 1 h / 20 °C 3.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C 4.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C 5.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C 6.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C 7.1: boron trichloride / dichloromethane / 0.67 h / 0 °C 8.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr 9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C 11.2: 1 h / 20 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C 12.2: 4.17 h / 0 - 20 °C 13.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C 14.1: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme

Yield

Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C
1.2: 2.5 h / -78 °C
2.1: dmap / acetonitrile / 1 h / 20 °C
3.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C
4.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C
5.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C
6.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C
7.1: boron trichloride / dichloromethane / 0.67 h / 0 °C
8.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C
11.2: 1 h / 20 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C
12.2: 4.17 h / 0 - 20 °C
13.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C
14.1: triethylamine / tetrahydrofuran / 1 h / 20 °C
View Scheme

: 69866-21-3
CC-1065

: C37H35N7O9

Conditions

Conditions	Yield
With water In aq. phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.0; Reagent/catalyst; Enzymatic reaction;

ANTIBIOTIC CC 1065 Chemical Properties

Product Name: Antibiotic CC 1065 (CAS NO.69866-21-3)

Molecular Formula: C₃₇H₃₃N₇O₈
Molecular Weight: 703.7g/mol
Mol File: 69866-21-3.mol
Density: 1.75 g/cm³
Surface Tension: 125.7 dyne/cm
XLogP3-AA: 2.4
H-Bond Donor: 6
H-Bond Acceptor: 8

ANTIBIOTIC CC 1065 Toxicity Data With Reference

1.	dni-mus:leu 4 µg/L	CNREA8 Cancer Research. 42 (1982),999.
2.	oms-mus:leu 45 µg/L	CNREA8 Cancer Research. 42 (1982),999.
3.	dni-ham:ovr 150 ng/L	CNREA8 Cancer Research. 42 (1982),3532.
4.	oms-ham:ovr 5 µg/L	CNREA8 Cancer Research. 42 (1982),3532.
5.	dnd-mam:lym 7400 nmol/L	CNREA8 Cancer Research. 42 (1982),999.
6.	ipr-mus LD50:6900 ng/kg	JANTAJ Journal of Antibiotics. 37 (1984),63.
7.	ivn-mus LD50:9 µg/kg	JANTAJ Journal of Antibiotics. 37 (1984),63.
8.	ivn-rbt LDLo:1 µg/kg	JANTAJ Journal of Antibiotics. 37 (1984),63.

ANTIBIOTIC CC 1065 Safety Profile

Deadly poison by intravenous and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NO_x.

ANTIBIOTIC CC 1065 Specification

Antibiotic CC 1065 ,its CAS NO. is 69866-21-3,the synonyms is Rachelmycin ; CC 1065 ; CCRIS 2174 ; NSC 298223 ; Benzo(1,2-b:4,3-b')dipyrrole-3(2H)-carboxamide, 7-((1,6-dihydro-4-hydroxy-5-methoxy-7-((4,5,8,8a-tetrahydro-7-
methyl-4-oxocyclopropa(c)pyrrolo(3,2-e)indol-2(1H)-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrol-3(2H)-yl)carbonyl)-
1,6-dihydro-4-hydroxy-5-methoxy-, (7bR)- .

Product Name

Rachelmycin

Synthetic route

ANTIBIOTIC CC 1065 Chemical Properties

ANTIBIOTIC CC 1065 Toxicity Data With Reference

ANTIBIOTIC CC 1065 Safety Profile

ANTIBIOTIC CC 1065 Specification

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