4-Propylbenzoyl chloride → N-(2-Oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-4-propyl-benzamide

HRID 620581Notes

Reaction equation

HRID 620581 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].[CH2:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)[CH2:21][CH3:22]>>[C:9]1([C:7]2[C:6]3[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=3[NH:4][C:3](=[O:19])[CH:2]([NH:1][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([CH2:20][CH2:21][CH3:22])=[CH:24][CH:25]=3)[N:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 1042934-Propylbenzoyl chlorideHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 14208261N-(2-Oxo-5-phenyl-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl)-4-propyl-benzamide

Procedure

The procedure of Example 134 was carried out using 3(RS)-amino-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (39.2 mg, 0.156 mmole) in place of 1,3-dihydro-3(RS)-amino-5-(2-fluorophenyl)-2H-1,4-benzodiazepin- 2-one and 4-n-propylbenzoyl chloride (28.5 mg, 0.156 mmole) in place of p-trifluoromethylbenzoyl chloride. The product was chromatographed on silica gel (15% (v/v) Et2O in CH2Cl2 elution). The combined product fractions were evaporated to dryness in vacuo and crystallized from Et2O to give the title compound which was dried in vacuo at 82° C.: (m.p.. 158°-162° C.).

Workup

  1. customThe product was chromatographed on silica gel (15% (v/v) Et2O in CH2Cl2 elution)
  2. customThe combined product fractions were evaporated to dryness in vacuo
  3. customcrystallized from Et2O

Sources & evidence

ORD record
ord-21dbd385506946d6931f7e4dd35bcfbb
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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