Ammonia acetate → 2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 79992

反応式

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]#[N:14])[CH2:10][CH:9]1[C:15](=O)[NH:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[NH3:32]>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([C:13]#[N:14])[CH2:10][CH:9]1[C:15]1[NH:32][C:18]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)=[CH:17][N:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

反応条件

温度: 110 °C

実験手順

A mixture of 2-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (1.05 g, 2.4 mmol) and ammonia acetate (3.7 g, 20 eq.) in Xylene (2 mL) was heated in microwave at 110° C. for 2 hours. The mixture was concentrated and purified by flash column chromatography (silica gel, 20 to 80% ethyl acetate/hexane) to give 2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (356 mg, containing 15% starting material, yield 35%). LCMS-ESI−: calc'd for C19H21BrN4O2: 417.30. Found: 418.9 (M+H+).

後処理

concentrationThe mixture was concentrated
custompurified by flash column chromatography (silica gel, 20 to 80% ethyl acetate/hexane)

出典と根拠

ORDレコード: ord-e61d547aa18f4aab85bb5b401fa443f6
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08841278B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

関連ノート