Product Name

  • Name

    Tolvaptan

  • EINECS 691-537-5
  • CAS No. 150683-30-0
  • Article Data18
  • CAS DataBase
  • Density 1.311 g/cm3
  • Solubility
  • Melting Point 219-222°C
  • Formula C26H25ClN2O3
  • Boiling Point 594.4 °C at 760 mmHg
  • Molecular Weight 448.949
  • Flash Point 313.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 150683-30-0 (Tolvaptan)
  • Hazard Symbols
  • Synonyms 7-Chloro-5-hydroxy-1-(2-methyl-4-(2-methylbenzoylamino)benzoyl)2,3,4,5-tetrahydro-1H-1-benzazepine;Benzamide, N-(4-((7-chloro-2,3,4,5-tetrahydro-5-hydroxy-1H-1-benzazepin-1-yl)carbonyl)-3-methylphenyl)-2-methyl-;N-[4-[(5R)-7-Chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl]-3-methylphenyl]-2-methylbenzamide;
  • PSA 69.64000
  • LogP 5.82110

Synthetic route

MOP-21826
137973-76-3

MOP-21826

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 0℃; for 2h;96%
With methanol; sodium tetrahydroborate at 20℃; for 5h;94%
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at -5 - 20℃; Solvent;94.2%
MOP-21826
137973-76-3

MOP-21826

A

C34H32ClN3O4

C34H32ClN3O4

B

C42H36ClN3O5

C42H36ClN3O5

C

C42H38ClN3O5

C42H38ClN3O5

D

C42H38ClN3O5

C42H38ClN3O5

E

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Stage #1: MOP-21826 With sodium tetrahydroborate In methanol for 1h;
Stage #2: With hydrogenchloride In methanol; water at 20℃;		A n/a
B n/a
C n/a
D n/a
E 90%
...Expand
(±)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol

(±)-7-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-ol

2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride
331947-69-4

2-methyl-4-(2-methylbenzoylamino)benzoic acid chloride

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
With 2,6-dimethylpyridine In N,N-dimethyl acetamide; water at 0℃; for 2h; Reagent/catalyst;72%
2,2-dimethyl-propionic acid 7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

2,2-dimethyl-propionic acid 7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 50℃; for 2h;
With sodium hydroxide; ethanol; water at 50℃; for 2h;
(rac)-7-chloro-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl pivalate
804498-94-0

(rac)-7-chloro-4-oxo-1,2,3,4-tetrahydronaphthalen-1-yl pivalate

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 96 percent / hydroxylamine hydrochloride; sodium acetate / ethanol; H2O / 2 h / Heating
2: PCl5 / CH2Cl2 / 2 h / 20 °C
3: acetic acid; Zn / 0.5 h / Heating
4: BH3*THF / tetrahydrofuran / 0.5 h / Heating
5: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
6: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
7: triethylamine / CH2Cl2 / 1 h / 20 °C
8: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethylpropionic acid 7-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
863762-10-1

2,2-dimethylpropionic acid 7-chloro-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
2: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
3: triethylamine / CH2Cl2 / 1 h / 20 °C
4: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethyl-propionic acid 7-chloro-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

2,2-dimethyl-propionic acid 7-chloro-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: BH3*THF / tetrahydrofuran / 0.5 h / Heating
2: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
3: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
4: triethylamine / CH2Cl2 / 1 h / 20 °C
5: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethylpropionic acid 4-[(E)-hydroxyimino]-7-chloro-1,2,3,4-tetrahydronaphthalen-1-yl ester
863762-02-1

2,2-dimethylpropionic acid 4-[(E)-hydroxyimino]-7-chloro-1,2,3,4-tetrahydronaphthalen-1-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: PCl5 / CH2Cl2 / 2 h / 20 °C
2: acetic acid; Zn / 0.5 h / Heating
3: BH3*THF / tetrahydrofuran / 0.5 h / Heating
4: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
5: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
6: triethylamine / CH2Cl2 / 1 h / 20 °C
7: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethyl-propionic acid 3,3,7-trichloro-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

2,2-dimethyl-propionic acid 3,3,7-trichloro-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: acetic acid; Zn / 0.5 h / Heating
2: BH3*THF / tetrahydrofuran / 0.5 h / Heating
3: 98 percent / triethylamine / CH2Cl2 / 1 h / 20 °C
4: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
5: triethylamine / CH2Cl2 / 1 h / 20 °C
6: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethylpropionic acid 7-chloro-1-(4-amino-2-methylbenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
863762-24-7

2,2-dimethylpropionic acid 7-chloro-1-(4-amino-2-methylbenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / CH2Cl2 / 1 h / 20 °C
2: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
2,2-dimethylpropionic acid 7-chloro-1-(2-methyl-4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester
863762-20-3

2,2-dimethylpropionic acid 7-chloro-1-(2-methyl-4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 82 percent / hydrochloric acid; SnCl2 / ethanol / 2 h / Heating
2: triethylamine / CH2Cl2 / 1 h / 20 °C
3: NaOH / ethanol; H2O / 2 h / 50 °C
View Scheme
4-chlorobenzenesulfonyl chloride
5202-89-1

4-chlorobenzenesulfonyl chloride

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 85 percent / pyridine / 20 °C
2.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C
3.1: t-BuOK / toluene / 0.5 h / Heating
3.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating
4.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
5.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
6.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
7.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
8.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1: sodium carbonate / acetonitrile / 5 h / 80 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C
3: potassium tert-butylate / toluene / 1 h / 120 °C
4: acetic acid; hydrogenchloride / water / 6 h / 100 °C
5: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C
6: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
7: sodium tetrahydroborate; methanol / 2 h / 0 °C
View Scheme
5-chloro-2-nitrobenzoic acid
2516-95-2

5-chloro-2-nitrobenzoic acid

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: 100 percent / K2CO3 / acetone / 0.5 h / Heating
2.1: SnCl2*2H2O; conc. HCl / ethanol / 20 °C
3.1: 85 percent / pyridine / 20 °C
4.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C
5.1: t-BuOK / toluene / 0.5 h / Heating
5.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating
6.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
7.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
8.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
9.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
10.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
2-methyl-4-nitrobenzoyl chloride
30459-70-2

2-methyl-4-nitrobenzoyl chloride

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
4: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / dichloromethane; water / pH 7 - 8
2.1: tin(ll) chloride / methanol / 16 h / 20 °C
3.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8
4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
4.2: pH 6 - 7
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
2.1: tin(IV) chloride / methanol / 16 h / 20 °C
3.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
4.2: pH 6.0 - 7.0
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium hydroxide / acetonitrile / 0.5 h / 10 °C
1.2: 5 h
2.1: methanol; tin(II) chloride dihdyrate / 23 h / 10 °C
3.1: magnesium hydroxide / dichloromethane; water / 0.5 h / 10 °C
3.2: 3 h
4.1: sodium tetrahydroborate; methanol / 1 h
View Scheme
2-methyl-4-nitrobenzoic acid
1975-51-5

2-methyl-4-nitrobenzoic acid

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SOCl2
2: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
3: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
4: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
5: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
methyl 5-chloro-2-nitrobenzoate
51282-49-6

methyl 5-chloro-2-nitrobenzoate

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: SnCl2*2H2O; conc. HCl / ethanol / 20 °C
2.1: 85 percent / pyridine / 20 °C
3.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C
4.1: t-BuOK / toluene / 0.5 h / Heating
4.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating
5.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
6.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
7.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
8.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
9.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one
160129-45-3

7-chloro-1,2,3,4-tetrahydro-5H-benzo[b]azepin-5-one

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
2: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
3: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
4: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / dichloromethane; water / pH 7 - 8
2.1: tin(ll) chloride / methanol / 16 h / 20 °C
3.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8
4.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
4.2: pH 6 - 7
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
2.1: tin(IV) chloride / methanol / 16 h / 20 °C
3.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
4.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
4.2: pH 6.0 - 7.0
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate; triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide; water / 8 h / 120 °C / 22502.3 Torr / Autoclave
2: iron; ammonium chloride / water; methanol / 6 h / 35 - 40 °C
3: pyridine / dichloromethane / 2 h / 0 - 10 °C
4: sodium tetrahydroborate; methanol / 1 h / 15 - 30 °C
View Scheme
Multi-step reaction with 4 steps
1.1: magnesium hydroxide / acetonitrile / 0.5 h / 10 °C
1.2: 5 h
2.1: methanol; tin(II) chloride dihdyrate / 23 h / 10 °C
3.1: magnesium hydroxide / dichloromethane; water / 0.5 h / 10 °C
3.2: 3 h
4.1: sodium tetrahydroborate; methanol / 1 h
View Scheme
N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester
247237-38-3

N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 94 percent / K2CO3 / dimethylformamide / 4 h / 120 °C
2.1: t-BuOK / toluene / 0.5 h / Heating
2.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating
3.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
4.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
5.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
6.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
7.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
7-chloro-1-(4-methylbenzenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one
193686-76-9

7-chloro-1-(4-methylbenzenesulfonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-5-one

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
2: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
3: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
4: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
5: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine
137977-97-0

1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
2: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
2.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
2.2: pH 6.0 - 7.0
View Scheme
1-(4-nitro-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine
137982-91-3

1-(4-nitro-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
2: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
3: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: tin(ll) chloride / methanol / 16 h / 20 °C
2.1: sodium hydrogencarbonate / dichloromethane / 0 - 5 °C / pH 7 - 8
3.1: sodium tetrahydroborate; methanol / 1 h / 20 °C
3.2: pH 6 - 7
View Scheme
Multi-step reaction with 3 steps
1.1: tin(IV) chloride / methanol / 16 h / 20 °C
2.1: sodium hydrogencarbonate / water; dichloromethane / 0 - 5 °C / pH 7.0 - 8.0
3.1: sodium tetrahydroborate / methanol / 1 h / 20 °C
3.2: pH 6.0 - 7.0
View Scheme
methyl 5-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate
247237-43-0

methyl 5-chloro-2-[N-(3-ethoxycarbonyl)propyl-N-p-toluenesulfonyl]aminobenzoate

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: t-BuOK / toluene / 0.5 h / Heating
1.2: 60 percent / conc. HCl / acetic acid / 5 h / Heating
2.1: 81 percent / polyphosphoric acid / 1.5 h / 80 - 100 °C
3.1: 32 percent / Et3N / CH2Cl2 / 2 h / 20 °C
4.1: 39 percent / SnCl2*2H2O; conc. HCl / ethanol / 20 °C
5.1: 53 percent / Et3N / CH2Cl2 / 1.5 h / 20 °C
6.1: 30 percent / NaBH4 / methanol / 1 h / 20 °C
View Scheme
C13H16ClNO4

C13H16ClNO4

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 20 °C
2: potassium tert-butylate / toluene / 1 h / 120 °C
3: acetic acid; hydrogenchloride / water / 6 h / 100 °C
4: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C
5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
6: sodium tetrahydroborate; methanol / 2 h / 0 °C
View Scheme
C21H21ClN2O7

C21H21ClN2O7

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium tert-butylate / toluene / 1 h / 120 °C
2: acetic acid; hydrogenchloride / water / 6 h / 100 °C
3: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C
4: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
5: sodium tetrahydroborate; methanol / 2 h / 0 °C
View Scheme
C20H17ClN2O6

C20H17ClN2O6

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; hydrogenchloride / water / 6 h / 100 °C
2: hydrogenchloride; tin(II) chloride dihdyrate / ethanol / 4 h / 20 °C
3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
4: sodium tetrahydroborate; methanol / 2 h / 0 °C
View Scheme
C18H16Cl2N2O4

C18H16Cl2N2O4

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: dichloromethane / 4.5 h / 20 °C / Reflux
2: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C
3: triethylamine / dichloromethane / 2.25 h / 20 °C
4: sodium tetrahydroborate; methanol / 5 h / 20 °C
View Scheme
4-chloro-aniline
106-47-8

4-chloro-aniline

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium carbonate / acetonitrile / 4 h / 80 °C
2: triethylamine / dichloromethane / 3 h / 20 °C
3: sodium hydroxide / 1.5 h / 50 °C
4: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux
5: dichloromethane / 4.5 h / 20 °C / Reflux
6: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C
7: triethylamine / dichloromethane / 2.25 h / 20 °C
8: sodium tetrahydroborate; methanol / 5 h / 20 °C
View Scheme
ethyl 4-(4-chlorophenylamino)butanoate

ethyl 4-(4-chlorophenylamino)butanoate

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: triethylamine / dichloromethane / 3 h / 20 °C
2: sodium hydroxide / 1.5 h / 50 °C
3: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux
4: dichloromethane / 4.5 h / 20 °C / Reflux
5: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C
6: triethylamine / dichloromethane / 2.25 h / 20 °C
7: sodium tetrahydroborate; methanol / 5 h / 20 °C
View Scheme
C20H21ClN2O5

C20H21ClN2O5

tolvaptan
150683-30-0

tolvaptan

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium hydroxide / 1.5 h / 50 °C
2: thionyl chloride / dichloromethane / 2 h / 20 °C / Reflux
3: dichloromethane / 4.5 h / 20 °C / Reflux
4: hydrogenchloride; tin(II) chloride dihdyrate / water; ethanol / 3 h / 20 °C
5: triethylamine / dichloromethane / 2.25 h / 20 °C
6: sodium tetrahydroborate; methanol / 5 h / 20 °C
View Scheme
Dibenzyl N,N-diisopropylphosphoramidite
108549-23-1

Dibenzyl N,N-diisopropylphosphoramidite

tolvaptan
150683-30-0

tolvaptan

C40H38ClN2O6P

C40H38ClN2O6P

Conditions
ConditionsYield
Stage #1: Dibenzyl N,N-diisopropylphosphoramidite; tolvaptan With 1H-tetrazole In dichloromethane at 20℃; for 2h;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -40 - 0℃; for 1h;		97.2%
Multi-step reaction with 2 steps
1: 2H-tetrazole / dichloromethane / 2 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C
View Scheme
tolvaptan
150683-30-0

tolvaptan

C26H26ClN2O6P
942619-74-1

C26H26ClN2O6P

Conditions
ConditionsYield
Stage #1: tolvaptan With triethylamine; trichlorophosphate In 1,2-dimethoxyethane at -15 - -12℃; for 2h;
Stage #2: With sodium hydroxide; water In 1,2-dimethoxyethane; toluene at 0 - 50℃;
Stage #3: With hydrogenchloride; water at 10℃; Product distribution / selectivity;		97%
Multi-step reaction with 3 steps
1: 2H-tetrazole / dichloromethane / 2 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C
3: 5%-palladium/activated carbon; hydrogen / ethanol / 0.17 h
View Scheme
Multi-step reaction with 2 steps
1.1: 1H-tetrazole / dichloromethane / 2 h / 20 °C
1.2: 1 h / -40 - 0 °C
2.1: 5%-palladium/activated carbon; hydrogen / ethanol
View Scheme
methanol
67-56-1

methanol

tolvaptan
150683-30-0

tolvaptan

C27H28ClN2O5P
942619-87-6

C27H28ClN2O5P

Conditions
ConditionsYield
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 0 - 20℃; for 0.5h;
Stage #2: methanol at 20℃; for 0.5h;		91%
tolvaptan
150683-30-0

tolvaptan

fluorodeoxytolvaptan

fluorodeoxytolvaptan

Conditions
ConditionsYield
With 1,3-bis(2,6-diisopropylphenyl)-2-fluoroimidazolium tetrafluoroborate; cesium fluoride In toluene at 80℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube;86%
tolvaptan
150683-30-0

tolvaptan

C26H24ClN2O6P(2-)*2Na(1+)

C26H24ClN2O6P(2-)*2Na(1+)

Conditions
ConditionsYield
Stage #1: tolvaptan With triethylamine; trichlorophosphate In 1,2-dimethoxyethane at -18 - -13℃; for 2h; Inert atmosphere; Large scale;
Stage #2: With water; sodium hydroxide In 1,2-dimethoxyethane at -3 - 30℃; for 0.5h; Inert atmosphere; Large scale;		86%
Multi-step reaction with 4 steps
1: 2H-tetrazole / dichloromethane / 2 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -40 - 0 °C
3: 5%-palladium/activated carbon; hydrogen / ethanol / 0.17 h
4: sodium hydroxide / methanol; water / 0.08 h / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: 1H-tetrazole / dichloromethane / 2 h / 20 °C
1.2: 1 h / -40 - 0 °C
2.1: 5%-palladium/activated carbon; hydrogen / ethanol
3.1: sodium hydroxide / methanol; water / 0.08 h / Cooling with ice
View Scheme
3-Hydroxypropionitrile
109-78-4

3-Hydroxypropionitrile

tolvaptan
150683-30-0

tolvaptan

C29H29ClN3O5P

C29H29ClN3O5P

Conditions
ConditionsYield
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 0.5h;
Stage #2: 3-Hydroxypropionitrile at 20℃; for 0.5h;		75%
tolvaptan
150683-30-0

tolvaptan

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} hexadecanoate
1094837-35-0

{7-chloro-1-[2-methyl-4-(2-methyl-benzoylamino)-benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl} hexadecanoate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;74%
tolvaptan
150683-30-0

tolvaptan

C26H26ClN2O5P

C26H26ClN2O5P

Conditions
ConditionsYield
Stage #1: tolvaptan With triethylamine; phosphorus trichloride In tetrahydrofuran at -10℃; for 2h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran at 0℃; Product distribution / selectivity;		60%
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 1h;
Stage #2: With water at 20℃; for 0.5h; Product distribution / selectivity;		24%
ethanol
64-17-5

ethanol

tolvaptan
150683-30-0

tolvaptan

C28H30ClN2O5P

C28H30ClN2O5P

Conditions
ConditionsYield
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 0 - 20℃; for 1h;
Stage #2: ethanol at 20℃; for 0.5h;		38%
methanol
67-56-1

methanol

tolvaptan
150683-30-0

tolvaptan

C28H30ClN2O6P

C28H30ClN2O6P

Conditions
ConditionsYield
Stage #1: tolvaptan With triethylamine; trichlorophosphate In tetrahydrofuran for 0.5h; Cooling with ice/methanol;
Stage #2: methanol With triethylamine In tetrahydrofuran for 0.5h;		33%
glycolic acid methyl ester
96-35-5

glycolic acid methyl ester

tolvaptan
150683-30-0

tolvaptan

C29H30ClN2O7P

C29H30ClN2O7P

Conditions
ConditionsYield
Stage #1: tolvaptan With pyridine; diphenyl hydrogen phosphite at 20℃; for 1h;
Stage #2: glycolic acid methyl ester at 20℃; for 12h;		20%

Tolvaptan Specification

1. Introduction of Tolvaptan

Tolvaptan, with the IUPAC Name of N-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)-3-methylphenyl]-2-methylbenzamide, is one kind of white powder. This chemical belongs to the Classification Code which include Treatment of congestive heart failure and hyponatremia [vasopressin V2 receptor antagonist]; Vasopressin V2 Receptor Antagonist.

2. Properties of Tolvaptan

Tolvaptan has the following properties: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 49.85; (3)Index of Refraction: 1.663; (4)Molar Refractivity: 126.96 cm3; (5)Molar Volume: 342.4 cm3; (6)Surface Tension: 59.7 dyne/cm; (7)Density: 1.311 g/cm3; (8)Flash Point: 313.3 °C; (9)Enthalpy of Vaporization: 93.18 kJ/mol; (10)Boiling Point: 594.4 °C at 760 mmHg; (11)Vapour Pressure: 5.64E-15 mmHg at 25°C.

3. Structure Descriptors of Tolvaptan

You could convert the following datas into the molecular structure:
(1).Smiles:c1cc(c(cc1)C)C(=O)Nc1ccc(C(=O)N2CCC[C@@H](c3c2ccc(c3)Cl)O)c(c1)C

Related Products

Hot Products

Post buying leads

About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia

Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog

©2008 LookChem.com,License: ICP

NO.:Zhejiang16009103

complaints:service@lookchem.com Desktop View