Triethylamine → 7,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanone

HRID 2184451ノート

反応式

HRID 2184451 の反応式
[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[NH:12][CH2:11][C:10]3=[CH:13][CH:14]=[CH:15][N:9]3[CH2:8][C:7]=2[CH:16]=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[Br:29])[C:23](Cl)=[O:24].C(N(CC)CC)C>ClCCl>[CH3:1][O:2][C:3]1[C:4]([O:17][CH3:18])=[CH:5][C:6]2[N:12]([C:23]([C:22]3[CH:26]=[CH:27][C:28]([Br:29])=[C:20]([CH3:19])[CH:21]=3)=[O:24])[CH2:11][C:10]3=[CH:13][CH:14]=[CH:15][N:9]3[CH2:8][C:7]=2[CH:16]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 3108382,3-dimethoxy-6,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepineHCID 70215344-Bromo-3-methylbenzoyl chloride

生成物 1

HCID 219477397,8-dimethoxy-(10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-(4-bromo-3-methyl-phenyl)-methanone収率 60.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 7,8-dimethoxy-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine of Step B (3.20 g) in dichloromethane (20 mL) was added 3-methyl-4-bromo benzoyl chloride (3.4 g, 1.1 equiv) and triethylamine (2.0 g, 1.5 equiv) and the mixture was stirred at room temperature overnight. The solvent was then removed in vacuo and the residue chromatographed on silica gel eluting with a solvent gradient from 5 to 50% ethyl acetate in petroleum ether to provide the title compounds as a yellow crystalline solid (3.5 g), m.p. 165-168° C.

後処理

  1. customThe solvent was then removed in vacuo
  2. customthe residue chromatographed on silica gel eluting with a solvent gradient from 5 to 50% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-fc24d08677fe4dde9b9c203b70e41e72
出典データセット
uspto-grants-2005_05
特許番号
US06900200B2

反応ノート

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