Sodium Carbonate → 5-Dehydro Tolvaptan

HRID 570903Notes

Reaction equation

HRID 570903 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([N:8]2[C:14]3[CH:15]=[CH:16][C:17]([Cl:19])=[CH:18][C:13]=3[C:12](=[O:20])[CH2:11][CH2:10][CH2:9]2)=[O:7])=[C:4]([CH3:23])[CH:3]=1.[CH3:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.C1CCCCC1.C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:19][C:17]1[CH:16]=[CH:15][C:14]2[N:8]([C:6](=[O:7])[C:5]3[CH:21]=[CH:22][C:2]([NH:1][C:27](=[O:28])[C:26]4[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=4[CH3:24])=[CH:3][C:4]=3[CH3:23])[CH2:9][CH2:10][CH2:11][C:12](=[O:20])[C:13]=2[CH:18]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 702762-Methylbenzoyl chlorideHCID 516892Sodium BicarbonateHCID 196082321-(4-Amino-2-methylbenzoyl)-7-chloro-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one

Product 1

HCID 113628435-Dehydro Tolvaptan

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

Typically, 1-(4-amino-2-methylbenzoyl)-7-chloro-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine is reacted with 2-methylbenzoylchloride in water immiscible solvent selected from methylene chloride, toluene or cyclohexane in the presence of aqueous inorganic base such as aqueous sodium bicarbonate or aqueous sodium carbonate to form a biphasic system to obtain 7-chloro-1-[2-methyl-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine.

Workup

  1. customto form a biphasic system

Sources & evidence

ORD record
ord-d1971ed5f8334533806a4a42995d9fff
Source dataset
uspto-grants-2015_05
Patent number
US09024015B2

Reaction notes

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