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

HRID 417743

반응식

HRID 417743 반응식
[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]

참가 물질

4

반응물 2

HCID 12432Ammonia acetateHCID 666213862-[2-(4-Bromo-phenyl)-2-oxo-ethylcarbamoyl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 666205592-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-cyano-pyrrolidine-1-carboxylic acid tert-butyl ester수율 35.5%

시약·촉매·용매 1

HCID 7237O-Xylene용매

반응 조건

온도
110 °C

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-e9833f50561b44028018834e8499befb
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088368B2

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