Cialis supplier | CasNO.171596-29-5

Name
Tadalafil
EINECS 200-835-2
CAS No. 171596-29-5
Article Data48
CAS DataBase
Density 1.51 g/cm³
Solubility
Melting Point 298-300 °C
Formula C₂₂H₁₉N₃O₄
Boiling Point 679.1 °C at 760 mmHg
Molecular Weight 389.411
Flash Point 364.5 °C
Transport Information
Appearance white to off-white cyrstalline solid
Safety 16-36/37
Risk Codes 11-20/21/22-36
Molecular Structure
Hazard Symbols F,Xn
Synonyms Pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione,6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)-;(6R,12aR)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione;GF 196960;Tadalafil [USAN];Tildenafil;Calais;(6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione;Adcirca;
PSA 74.87000
LogP 2.08710

Synthetic route

: C22H19ClN2O5*(x)ClH

: 74-89-5
methylamine

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In dichloromethane at 0 - 5℃; for 3h; Temperature; Solvent;	99.3%

: 74-89-5
methylamine

: 171489-59-1
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃;	95%
In N,N-dimethyl-formamide at 20℃; for 10h;	95%
In methanol for 3h; Reflux; Large scale;	95.3%

: (6R,12aR)-6-(3,4-dihydroxyphenyl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2'-1,6]-pyrido[3,4-b]indole-1,4-dione

: 74-95-3
1,2-dibromomethane

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 60℃; for 6h;	95%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 8h;	93%

: 1224724-00-8
(1R,3R)-methyl-1,2,3,4-tetrahydro-2-(2-(benzyl(methyl)amino)acetyl)-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With hydrogen; Raney Ni In ISOPROPYLAMIDE at 80℃; under 2280.15 Torr; for 22h; Product distribution / selectivity;	94%

: 171489-59-1
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With methylamine In dichloromethane for 2h;	93.5%
With methylamine In water for 20h; Ionic liquid;	355 mg

: 52605-49-9
sarcosine ethyl ester hydrochloride

: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With potassium carbonate In ethylene glycol at 110℃; Solvent; Reagent/catalyst; Temperature; Green chemistry;	92.7%

: 749864-18-4
1-benzo[1,3]dioxol-5-yl-2-{[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-acetyl}-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With piperidine In N,N-dimethyl-formamide at 20℃; for 1h;	92%

: C22H20N4O3

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: C22H20N4O3 With sulfuric acid In isopropyl alcohol for 12h; Reflux; Stage #2: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 8h; Temperature;	91.2%

: (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid

: 74-89-5
methylamine

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In tetrahydrofuran; water at 50℃; Solvent; Temperature;	91%

: 107-97-1
sarcosine

: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: sarcosine; (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride With triethylamine In tetrahydrofuran at 30℃; for 0.333333h; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 0.5h; Solvent; Reagent/catalyst; Temperature; Further stages;	90.54%

: 120-57-0
piperonal

: C15H19N3O3*ClH

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In isopropyl alcohol at 80℃; for 16h; Solvent; Temperature;	58.2%

: 74-89-5
methylamine

: 171489-59-1
methyl (1R,3R)-1-(3,4-methylenedioxyphenyl)-2-chloroacetyl-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indol-3-carboxylate

A: 171596-27-3
(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

B: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In methanol at 50℃; for 16h;	A 1.1% B 54%

...Expand

: 474668-76-3
(1R,3R)-1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid hydrochloride

: 52605-49-9
sarcosine ethyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 50 - 55℃; for 10h; Large scale reaction;	52.6%

: 951661-81-7
(1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -50 - -35℃; for 2 - 6h; Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate at -40 - 30℃; Product distribution / selectivity;	48%
Stage #1: (1R,3R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-N-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxamide With n-butyllithium In tetrahydrofuran; hexane at -40 - -35℃; for 2.5h; Stage #2: With ammonium chloride In tetrahydrofuran; hexane; water; ethyl acetate at -40 - 30℃; Product distribution / selectivity;

: 120-57-0
piperonal

: 5241-64-5
Boc-D-Trp-OH

: 79-04-9
chloroacetyl chloride

: 74-89-5
methylamine

A: 171596-28-4
(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione

B: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Stage #1: Boc-D-Trp-OH With dmap; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Microwave irradiation; Stage #2: piperonal With trifluoroacetic acid In chloroform for 0.5h; Pictet-Spengler cyclisation; Microwave irradiation; Stage #3: chloroacetyl chloride; methylamine Further stages;	A 45% B 32%

...Expand

: 120-57-0
piperonal

rhodaninoic acid: rhodaninoic acid

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C 2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C 3: 54 percent / methanol / 16 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 85 percent / aq.HCl / methanol / 36 h / Heating 2: 78 percent / NaHCO3 / CH2Cl2; H2O 3: 88 percent / CHCl3; ethanol / 7 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h 2: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C 3: 92 percent / methanol / 16 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h 2: DMAP; basic alumina / CH2Cl2 / 2 h / -25 - 20 °C 3: 92 percent / piperidine / dimethylformamide / 1 h / 20 °C View Scheme

: 14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8
(R)-(+)-tryptophan methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 25 percent / TFA / methanol; CH2Cl2 / 60 h / 20 °C 2: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C 3: 54 percent / methanol / 16 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 85 percent / aq.HCl / methanol / 36 h / Heating 2: 78 percent / NaHCO3 / CH2Cl2; H2O 3: 88 percent / CHCl3; ethanol / 7 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 95 percent / Et3N; MgSO4 / CH2Cl2 / 24 h 2: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C 3: 92 percent / methanol / 16 h / 50 °C View Scheme

: 171596-41-1
(1R,3R)-methyl 1,2,3,4-tetrahydro-1-(3,4-methylenedioxyphenyl)-9H-pyrido[3,4-b]indole-3-carboxylate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / sodium bicarbonate / CH2Cl2 / 1 h / 0 °C 2: 54 percent / methanol / 16 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 93 percent / NaHCO3 / CHCl3 / 20 °C 2: 77 percent / ethanol / Heating View Scheme

: (1R,3R)-1-benzo[1,3]dioxol-5-yl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaHCO3 / CH2Cl2; H2O 2: 88 percent / CHCl3; ethanol / 7 h / Heating View Scheme

: (R)-2-{[1-Benzo[1,3]dioxol-5-yl-meth-(E)-ylidene]-amino}-3-(1H-indol-3-yl)-propionic acid methyl ester

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 43 percent / DMAP / CH2Cl2 / 2 h / 20 °C 2: 92 percent / methanol / 16 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: DMAP; basic alumina / CH2Cl2 / 2 h / -25 - 20 °C 2: 92 percent / piperidine / dimethylformamide / 1 h / 20 °C View Scheme

: 120-57-0
piperonal

glycocoll ester: glycocoll ester

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 42 percent / TFA / CH2Cl2 / 20 °C 2: 93 percent / NaHCO3 / CHCl3 / 20 °C 3: 77 percent / ethanol / Heating View Scheme

: 4299-70-1, 7303-49-3, 22032-65-1
D-Tryptophan methyl ester

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 42 percent / TFA / CH2Cl2 / 20 °C 2: 93 percent / NaHCO3 / CHCl3 / 20 °C 3: 77 percent / ethanol / Heating View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water; toluene / 15 h / Reflux; Large scale 2.1: triethylamine / dichloromethane / 0.17 h / 20 °C / Large scale 2.2: 1 h / 20 °C / Large scale 3.1: methanol / 3 h / Reflux; Large scale View Scheme
Multi-step reaction with 3 steps 1: isopropyl alcohol / 10 h / 70 - 80 °C / Large scale 2: triethylamine / chloroform / 2 h / 20 - 30 °C 3: methylamine / dichloromethane / 2 h View Scheme

: 1321600-91-2
methyl 1-(benzo[d][1,3]dioxol-5-yl)-2-(2-chloroacetyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

: 593-51-1
methylamine hydrochloride

A: 171596-28-4
(6S,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,12,12a tetrahydropyrazino [1',2':1,6] pyrido[3,4b] indole1,4(6H,7H)-dione

B: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With triethylamine In methanol Reflux;

...Expand

: 120-57-0
piperonal

: 14907-27-8, 5619-09-0, 7524-52-9, 26988-71-6, 41222-70-2, 67557-19-1, 109492-62-8
(R)-(+)-tryptophan methyl ester hydrochloride

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 3 h / 85 °C 1.2: 1 h / 0 - 10 °C 2.1: water; tetrahydrofuran / 1 h / 55 °C / Inert atmosphere View Scheme

: 120-57-0
piperonal

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 0.25 h / 110 °C 2: triethylamine / water; tetrahydrofuran / 2 h / 0 - 10 °C / Inert atmosphere 3: water; tetrahydrofuran / 1 h / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: 0.25 h / 110 °C 2: triethylamine / tetrahydrofuran; water / 2 h / 0 - 10 °C / Inert atmosphere 3: tetrahydrofuran; water / 1 h / 55 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: acetonitrile / 105 °C / Autoclave 2: sodium carbonate / acetonitrile; water / 5 - 10 °C 3: water; isopropyl alcohol / 110 - 120 °C View Scheme

: N-Boc-D-tryptophan

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / Inert atmosphere 1.2: 1 h / -20 - 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C 3.1: toluene / 8 h / 110 °C View Scheme

: C24H25N3O5

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
In toluene at 110℃; for 8h;	0.39 g

: 120-57-0
piperonal

: 1422164-52-0
(R)-ethyl 2-(2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)-N-methylpropanamido)acetate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C 2: toluene / 8 h / 110 °C View Scheme

: 5241-64-5
Boc-D-Trp-OH

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine / tetrahydrofuran / 0.33 h / -20 °C / Inert atmosphere 1.2: 0.5 h / -20 °C / Inert atmosphere 2.1: 4-methyl-morpholine / tetrahydrofuran / Inert atmosphere 2.2: 1 h / -20 - 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / toluene / 15 h / 45 - 50 °C 4.1: toluene / 8 h / 110 °C View Scheme

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 171596-27-3
(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide; isopropyl alcohol at 83℃; for 5h;	98%

: 81-04-9
naphthalene-1,5-disulfonate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione naphthalene-1,5-disulfonic acid salt

Conditions

Conditions	Yield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;	95.4%

: 69-72-7
salicylic acid

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione salicylic acid salt

Conditions

Conditions	Yield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;	94.81%

: 17199-29-0
(S)-Mandelic acid

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione mandelic acid salt

Conditions

Conditions	Yield
In Isopropyl acetate at 45℃; for 48h; pH=2 - 3; Solvent;	94.25%

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 1021702-43-1
(6R,12aS)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-3,3,12a-trideuterio-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With water-d2; potassium carbonate In tetrahydrofuran; dimethylsulfoxide-d6 at 65℃; for 16h;	94%

: 141-82-2
malonic acid

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 1242099-10-0
C3H4O4*C22H19N3O4

Conditions

Conditions	Yield
In ethyl acetate for 5h;	85%
In acetonitrile Product distribution / selectivity;
In acetonitrile at 25℃; for 0.5h;

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 1220393-12-3
3-((2-(benzo[d][1,3]dioxole-5-carbonyl)-1H-indol-3-yl)methyl)-1-methylpiperazine-2,5-dione

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; water; tetramethlyammonium chloride In dimethyl sulfoxide at 40℃; for 7h;	79%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; water at 20℃; for 8h; Product distribution / selectivity;

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: C22H19N3O5

Conditions

Conditions	Yield
With N-Bromosuccinimide; acetic acid at 50℃; for 5h; Reagent/catalyst;	78%

: 696-63-9
4-Methoxybenzenethiol

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: (6R)-6-(6-((4-methoxyphenyl)thio)benzo[d][1,3]dioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With tetrabutylammonium tetrafluoroborate for 4.5h; Electrolysis; Inert atmosphere; Sealed tube; regioselective reaction;	65%

: 456-24-6
2-Fluoro-5-nitropyridine

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: (6R,12aR)-6-(benzo[d][1,3]dioxol-5-yl)-2-methyl-7-(5-nitropyridin-2-yl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 40h; Inert atmosphere;	61%

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: C22H15(2)H4N3O4

Conditions

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;	46%

: 2,8-difluoro-5-(trifluoromethyl)-5Hdibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: C23H18F3N3O4

Conditions

Conditions	Yield
With [(Tp)NiIV(CF3)3] In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	43%

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: C22H19N3O5

Conditions

Conditions	Yield
With tert.-butylnitrite; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 15h; Irradiation;	42%

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 11-benzo[1,3]dioxol-5-yl-3-methyl-2,3,4a,11-tetrahydro-10H-3,10,11a-triaza-benzo[b]fluorene-1,4,5-trione

Conditions

Conditions	Yield
With potassium superoxide; 18-crown-6 ether In N,N-dimethyl-formamide at 25℃; for 6h; Winterfeldt oxidation;	38%
Multi-step reaction with 2 steps 1: O2; KOtBu / dimethylformamide; tetrahydrofuran / 4 h 2: 16.2 mg / PyBrOP; di-isopropylethylamine / dimethylformamide; tetrahydrofuran / 16 h / 25 °C View Scheme

: 171596-29-5
(6R,12aR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)-pyrazino[2',1':6,1]pyrido[3,4-b]indole-1,4-dione

: 422311-80-6
(6R,12aR)-6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6] pyrido[3,4-b]indole-1,4-dithione

Conditions

Conditions	Yield
With Lawessons reagent In tetrahydrofuran at 20℃; for 72h;	25%

Cialis Chemical Properties

The Molecular Structure of Tadalafil (CAS NO.171596-29-5):

Empirical Formula: C₂₂H₁₉N₃O₄
Molecular Weight: 389.404
Appearance: Off-White Cyrstalline Solid
Nominal Mass: 389 Da
Average Mass: 389.404 Da
Monoisotopic Mass: 389.137556 Da
Index of Refraction: 1.758
Molar Refractivity: 105.27 cm³
Molar Volume: 256.2 cm³
Surface Tension: 81.5 dyne/cm
Density: 1.51 g/cm³
Flash Point: 364.5 °C
Enthalpy of Vaporization: 99.67 kJ/mol
Boiling Point: 679.1 °C at 760 mmHg
Vapour Pressure: 2.67E-18 mmHg at 25°C
Melting Point: 298-300°C
Product Categories: Active Pharmaceutical Ingredients;Cnbio;Erectile Dysfunction;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's
InChI: InChI=1/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1
Smiles: C1N(C([C@H]2Cc3c([C@H](N2C1=O)c1ccc2c(c1)OCO2)[nH]c1ccccc31)=O)C

Cialis History

Tadalafil (CAS NO.171596-29-5) was discovered by Glaxo Wellcome (now GlaxoSmithKline) under a partnership between Glaxo and ICOS to develop new drugs that began in August 1991. In December 2003, after sildenafil (Viagra) and vardenafil (Levitra),the Food and Drug Administration approved tadalafil (as Cialis) for sale in the United States as the third ED prescription drug pill. Then in May 2009,Tadalafil was approved in the United States for the treatment of pulmonary arterial hypertension and is currently under regulatory review in other regions for this condition.

Cialis Uses

Tadalafil (CAS NO.171596-29-5) can be used for the treatment of erectile dysfunction under the name Cialis. Recently Tadalafil (CAS NO.171596-29-5) has been approved for the treatment of pulmonary arterial hypertension and other onditions.

Cialis Safety Profile

The most common side effects of tadalafil are: are headache, indigestion, flushing,back pain, muscle aches and stuffy or runny nose. These side effects reflect the ability of PDE5 inhibition to vasodilate (cause blood vessels to widen), these usually go away after a few hours. Back pain and muscle aches maybe occur 12 to 24 hours after taking the drug,and the symptom usually disappears after 48 hours.

Cialis Specification

Tadalafil (CAS NO.171596-29-5) is the main raw materials of Cialis,compare with Sildenafil,Tadalafil have less side effects, after taking two days,30% of people have muscles ache feeling (mainly waist and legs). It is also called as Tadalafil [USAN] ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-methylenedioxyphenyl)pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione ; Adcirca ; Cialis ; Tadalafil ; Tadalafil Lilly ;Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R,12aR)- ; Pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, 6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-, (6R-trans)- .

Product Name

Tadalafil

Synthetic route

Cialis Chemical Properties

Cialis History

Cialis Uses

Cialis Safety Profile

Cialis Specification

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