4-Cyanobenzoyl chloride → 4-Cyano-N-(2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide

HRID 620590Notes

Reaction equation

HRID 620590 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[NH:4][C:3]1=[O:19].[C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)#[N:21]>>[C:20]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][CH:2]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3]2=[O:19])=[O:27])=[CH:24][CH:23]=1)#[N:21]

Participants

3

Reactant 2

HCID 801724-Cyanobenzoyl chlorideHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 142082674-Cyano-N-(2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepin-3-yl)-benzamide

Procedure

The procedure of Example 134 was carried out employing equivalent amounts of 1,3-dihydro-3-(RS)-amino-5-phenyl-2H-1,4-benzodiazepin-2-one and 4-cyanobenzoylchloride. The product was purified by chromatography on silica gel (5% (v/v) Et2O in CH2Cl2 elution). The combined product fractions were evaporated to dryness in vacuo and crystallized to give the title compound which was dried at 65° C.

Workup

  1. customThe product was purified by chromatography on silica gel (5% (v/v) Et2O in CH2Cl2 elution)
  2. customThe combined product fractions were evaporated to dryness in vacuo
  3. customcrystallized

Sources & evidence

ORD record
ord-9ac063e59f444b819d615fc323519d1f
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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