2-Naphthoyl chloride → HCID 14208214, compound

HRID 620580Notes

Reaction equation

HRID 620580 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].[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:30](Cl)=[O:31]>>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[C:30]([NH: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])=[O:31]

Participants

3

Reactant 2

HCID 752462-Naphthoyl chlorideHCID 42596493-Amino-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

Product 1

HCID 14208214HCID 14208214, compound

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 2-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 CH2Cl2 /EtOAc to give the title compound which was dried in vacuo at 82° C.: (m.p. 293°-294° 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 CH2Cl2 /EtOAc

Sources & evidence

ORD record
ord-55a4d95c954f4ced88dfd8f49caf3a60
Source dataset
uspto-grants-1989_04
Patent number
US04820834

Reaction notes

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