Diisopropylethylamine → (E)-tert-butyl (2-(3-(imidazo[1,2-a]pyridin-3-yl)acrylamido)phenyl)carbamate

HRID 1850045노트

반응식

HRID 1850045 반응식
C(N(C(C)C)CC)(C)C.[N:10]1[CH:11]=[C:12](/[CH:19]=[CH:20]/[C:21]([OH:23])=O)[N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12.[C:24]([O:28][C:29](=[O:38])[NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH2:37])([CH3:27])([CH3:26])[CH3:25].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>ClCCl>[N:10]1[CH:11]=[C:12](/[CH:19]=[CH:20]/[C:21]([NH:37][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[NH:30][C:29](=[O:38])[O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:23])[N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 39196020(E)-3-(imidazo[1,2-a]pyridin-3-yl)acrylic acid

생성물 1

HCID 68349151(E)-tert-butyl (2-(3-(imidazo[1,2-a]pyridin-3-yl)acrylamido)phenyl)carbamate수율 33%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Diisopropylethylamine (DIPEA, 0.34 g, 2.63 mmol) was added to a solution of (E)-3-(imidazo[1,2-a]pyridin-3-yl)acrylic acid (0.17 g, 0.88 mmol) in 20 mL of dichloromethane (DCM). After addition of tert-butyl-2-aminophenylcarbamate (0.22 g, 1.65 mmol) and 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 0.43 g, 1.14 mmol) the reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. After completion of the reaction as indicated by HPLC, the reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) and brine. It was dried over Na2SO4, filtered and evaporated to give crude (E)-tert-butyl (2-(3-(imidazo[1,2-a]pyridin-3-yl)acrylamido)phenyl)carbamate. The solid was washed with ethyl acetate (50 mL) and saturated NaHCO3 gave pure product as a light colored solid (0.11 g). ES+(M+H)+379.

후처리

  1. customAfter completion of the reaction
  2. washthe reaction mixture was washed with saturated sodium bicarbonate (NaHCO3) and brine
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give crude (E)-tert-butyl (2-(3-(imidazo[1,2-a]pyridin-3-yl)acrylamido)phenyl)carbamate
  7. washThe solid was washed with ethyl acetate (50 mL) and saturated NaHCO3

출처 및 근거

ORD 기록
ord-51ef5ca8af164ed6b0c94028de6f33a5
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957066B2

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