1-Naphthalenecarbonyl chloride → 1,3-Dihydro-3(RS)-(1-naphthoylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 620584Notes

Reaction equation

HRID 620584 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]1([C:30](Cl)=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1>>[C:20]1([C:30]([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:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 701461-Naphthalenecarbonyl chlorideHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 142082151,3-Dihydro-3(RS)-(1-naphthoylamino)-5-phenyl-2H-1,4-benzodiazepin-2-one

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 1-naphthoyl chloride (29.7 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 65° C.: (m.p. 162°-167° 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-88ac715f32394c0baa6417acb65a6585
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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