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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
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HRID 1468065 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane
용매

실험 절차

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%)

후처리

  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

출처 및 근거

ORD 기록
ord-babe042881d84ee29386b320832c24a2
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09000175B2

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