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

HRID 1850045ノート

反応式

HRID 1850045 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-51ef5ca8af164ed6b0c94028de6f33a5
出典データセット
uspto-grants-2015_02
特許番号
US08957066B2

反応ノート

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