Water → Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionate

HRID 2370941ノート

反応式

HRID 2370941 の反応式
[H-].[Na+].[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Br[CH2:23][C:24]#[C:25][CH3:26].O>CN(C=O)C>[NH2:3][C:4]1[N:9]=[CH:8][C:7]([CH2:10][CH:11]([C:17]2[N:18]=[CH:19][N:20]([CH2:23][C:24]#[C:25][CH3:26])[CH:21]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 178470993HCID 178470993、化合物

生成物 1

HCID 69331513Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionate収率 39%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

11 mg (0.23 mmol, 50%) of sodium hydride were added to a solution of 60 mg (0.23 mmol) of ethyl 3-(6-aminopyridin-3-yl)-2-(1H-imidazol-4-yl)propionate (example 1g) in 0.5 ml of DMF at RT and stirred for 1 h. Then 31 mg (37 μl, 0.23 mmol) of 1-bromo-2-butine were added, and the mixture was stirred at RT for 1 h. 1 ml of water was then added and the mixture was extracted with EA. The organic phase was dried over Na2SO4, filtered and concentrated. Chromatography of the residue on silica gel afforded 28 mg of the title compound.

後処理

  1. stirringthe mixture was stirred at RT for 1 h
  2. extractionthe mixture was extracted with EA
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-df2fdcbaa70d4f1c8ed1c6542051fd19
出典データセット
uspto-grants-2014_04
特許番号
US08710232B2

反応ノート

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