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Triethylamine → tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate

HRID 1468065
ノート
印刷プレビュー

反応式

HRID 1468065 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([O:16][CH:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[S:14][CH:15]=1)[CH:6]=[CH:5]2.C(N(CC)CC)C.Cl[CH2:38][CH2:39][O:40][CH:41]=[O:42]>ClCCl>[CH2:39]([O:40][C:41]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[N:12]=[C:13]([O:16][CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]3)[S:14][CH:15]=1)[CH:6]=[CH:5]2)=[O:42])[CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2467482-Chloroethyl formateHCID 67616897tert-Butyl 4-((4-(5-amino-1H-indol-1-yl)thiazol-2-yl)oxy)-piperidine-1-carboxylate

生成物 1

HCID 67632626tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate収率 9.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a stirred solution of tert-butyl 4-((4-(5-amino-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate (intermediate-35) (0.100 g, 0.214 mmol) in dichloromethane (4 mL), triethylamine (0.036 g, 0.362 mmol), and chloroethylformate (0.026 g, 0.214 mmol) were added at 0° C. and stirred at room temperature for 10 minutes. The reaction was quenched with water and the mixture was extracted with dichloromethane. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to give tert-butyl 4-((4-(5-((ethoxycarbonyl)amino)-1H-indol-1-yl)thiazol-2-yl)oxy)piperidine-1-carboxylate (0.010 g, 8.5%)

後処理

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with dichloromethane
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography

出典と根拠

ORDレコード
ord-babe042881d84ee29386b320832c24a2
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000175B2

反応ノート

読み込み中…

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