1,1'-Carbonyldiimidazole → 3-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamide

HRID 14224ノート

反応式

HRID 14224 の反応式
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=O)=[CH:10][CH:11]=2)[N:6]([CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:32][C@@H:33]([CH2:47][C:48]1[CH:53]=[C:52]([F:54])[CH:51]=[C:50]([F:55])[CH:49]=1)[C@H:34]([OH:46])[CH2:35][NH:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[CH:39]=1>ClCCl>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:32][C@@H:33]([CH2:47][C:48]3[CH:49]=[C:50]([F:55])[CH:51]=[C:52]([F:54])[CH:53]=3)[C@H:34]([OH:46])[CH2:35][NH:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][CH3:45])[CH:39]=3)=[O:15])=[CH:10][CH:11]=2)[N:6]([CH2:16][CH2:17][CH2:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 210857003-acetyl-1-butyl-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 575082453-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamide収率 77.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Acetyl-1-butyl-1H-indole-6-carboxylic acid (0.322 g) was dissolved in dichloromethane (15 mL). 1,1′-Carbonyldiimidazole was added (0.171 g). The mixture was stirred for 2 h and then a mixture of (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (0.250 g) in dichloromethane (15 mL) was added. After stirring overnight, the mixture was partitioned between dichloromethane, water, and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel using MeOH/dichloromethane (4/96) to give 3-acetyl-1-butyl-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-1H-indole-6-carboxamide (0.335 g). MS (ESI+) for C34H39F2N3O3+H1 m/z 576.30 (M+H)+.

後処理

  1. additionwas added
  2. stirringAfter stirring overnight
  3. customthe mixture was partitioned between dichloromethane, water, and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

出典と根拠

ORDレコード
ord-3e55af888bed43239d72fd09885e2e11
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

反応ノート

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