Sodium Cyanide → Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

HRID 1882364노트

반응식

HRID 1882364 반응식
C(O[C:4](=[O:23])[CH2:5][N:6]1[CH2:10][CH2:9][N:8]([C:11]2[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=2)[C:7]1=[O:22])C.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.[C-]#N.[Na+]>ClCCl>[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:4](=[O:23])[CH2:5][N:6]2[CH2:10][CH2:9][N:8]([C:11]3[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=3)[C:7]2=[O:22])=[CH:27][CH:26]=1

참가 물질

5

반응물 3

HCID 8929Sodium CyanideHCID 673264-FluorobenzylamineHCID 57919757Ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

생성물 1

HCID 57919793Ethyl 2-(3-(2-(4-fluorobenzylamino)-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A mixture of ethyl 2-(3-(2-ethoxy-2-oxoethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate (0.43 g, 1.25 mmol), 4-fluorobenzylamine (3 mL) and catalytic amount of sodium cyanide was stirred at 80° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature, diluted with dichloromethane (25 mL) and filtered. The solid was washed with dichloromethane and hexanes on the filter. The filtrate was filtered again, and the solid was washed with hexanes. The combined material was dried to afford the title compound as a colorless solid (0.45 g, 86%): 1H NMR (300 MHz, CDCl3) δ 7.28-7.20 (m, 2H), 7.05-6.97 (m, 2H), 6.42 (br s, 1H), 4.42 (d, J=5.7 Hz, 2H), 4.29 (q, J=7.1 Hz, 2H), 4.19-4.10 (m, 2H), 3.99 (s, 2H), 3.77-3.70 (m, 2H), 2.62 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 421.2 (M+1).

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. washThe solid was washed with dichloromethane and hexanes on the filter
  4. filtrationThe filtrate was filtered again
  5. washthe solid was washed with hexanes
  6. customThe combined material was dried

출처 및 근거

ORD 기록
ord-a691abfff44b454cb867c03d16e2bdb2
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318949B2

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