1-butyl-4-(1,3-oxazol-2-yl)-1H-indole-6-carboxylic acid → 1-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-4-(1,3-oxazol-2-yl)-1H-indole-6-carboxamide

HRID 348970ノート

反応式

HRID 348970 の反応式
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:17]3[O:18][CH:19]=[CH:20][N:21]=3)[CH:10]=[C:11]([C:14]([OH:16])=O)[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].[NH2:22][C@@H:23]([CH2:37][C:38]1[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([F:45])[CH:39]=1)[C@H:24]([OH:36])[CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH3:35])[CH:29]=1>C(Cl)Cl>[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([C:17]3[O:18][CH:19]=[CH:20][N:21]=3)[CH:10]=[C:11]([C:14]([NH:22][C@@H:23]([CH2:37][C:38]3[CH:39]=[C:40]([F:45])[CH:41]=[C:42]([F:44])[CH:43]=3)[C@H:24]([OH:36])[CH2:25][NH:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([CH2:34][CH3:35])[CH:29]=3)=[O:16])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 210851691-butyl-4-(1,3-oxazol-2-yl)-1H-indole-6-carboxylic acidHCID 57487282(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

生成物 1

HCID 575129651-Butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-4-(1,3-oxazol-2-yl)-1H-indole-6-carboxamide収率 23.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

実験手順

To a mixture of 1-butyl-4-(1,3-oxazol-2-yl)-1H-indole-6-carboxylic acid (0.2 g) in methylene chloride (20 mL) was added 1,1-carbonyldiimidazole (0.114 g). The mixture was stirred at room temperature for 1 h at which time (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.265 g) dissolved in methylene chloride (10 mL) was added. The mixture was stirred at room temperature for 18 h then poured into methylene chloride (50 mL), washed with water followed by brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 65% methylene chloride, 30% hexanes, and 5% methanol as eluent to give 0.0985 g of the title compound: MS (ESI+) for C35H38F2N4O3 m/z 601.99 (M+H)+.

後処理

  1. additionwas added
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-10404e80df284cbdb3324993fe62bec9
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

反応ノート

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