Water → HCID 66733412, compound

HRID 1184646

Reaction equation

HRID 1184646 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([C:18]([N:20]2[C:26]3[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]=3[CH:24]([OH:32])[CH2:23][CH2:22][CH2:21]2)=[O:19])=[C:15]([CH3:17])[CH:16]=1)=[O:9].N1C=CC=CC=1.[Cl:39][CH2:40][CH2:41][CH2:42][C:43](Cl)=[O:44].O>ClCCl>[Cl:39][CH2:40][CH2:41][CH2:42][C:43]([O:32][CH:24]1[CH2:23][CH2:22][CH2:21][N:20]([C:18](=[O:19])[C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=3[CH3:1])=[CH:16][C:15]=2[CH3:17])[C:26]2[CH:27]=[CH:28][C:29]([Cl:31])=[CH:30][C:25]1=2)=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 216237Tolvaptan

Product 1

HCID 66733412HCID 66733412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tolvaptan (10.0 g, 22.3 mmol) was dispersed in dichloromethane (100 ml). Pyridine (2.7 ml) was added thereto, and the mixture was stirred. 4-Chlorobutyric acid chloride (3.74 ml) was gradually added to the obtained mixture, and the mixture was stirred at room temperature over night. The reactant was then poured into water, and the mixture was extracted with dichloromethane, washed with a sodium hydrogen sulfate aqueous solution, dried over magnesium sulfate. After filtration and concentration under reduced pressure, the resulted residue was crystallized with diethyl ether. The resulted crystals were collected by filtration, and dried to obtain 10.7 g of 7-chloro-1-[2-methyl-4-(2-methylbenzamido)benzoyl]-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl 4-chlorobutyrate as white powder.

Workup

  1. stirringthe mixture was stirred at room temperature over night
  2. extractionthe mixture was extracted with dichloromethane
  3. washwashed with a sodium hydrogen sulfate aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure
  6. customthe resulted residue was crystallized with diethyl ether
  7. filtrationThe resulted crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-082eedab464b4964a3a154191056b482
Source dataset
uspto-grants-2014_03
Patent number
US08669229B2

Linked notes

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