4-Fluorobenzylamine → 6-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid 4-fluoro-benzylamide

HRID 458694노트

반응식

HRID 458694 반응식
C(O[C:4]([C:6]1[N:7]=[C:8]2[NH:16][C:15](=[O:17])[CH2:14][N:9]2[C:10](=[O:13])[C:11]=1[OH:12])=[O:5])C.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1>C(O)C.CN(C)C=O>[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:4]([C:6]2[N:7]=[C:8]3[NH:16][C:15](=[O:17])[CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[OH:12])=[O:5])=[CH:21][CH:20]=1

참가 물질

5

반응물 2

HCID 673264-FluorobenzylamineHCID 1359709526-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl ester

생성물 1

HCID 1355082456-Hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid 4-fluoro-benzylamide수율 34.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of intermediate 5, 6-hydroxy-2,5-dioxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyrimidine-7-carboxylic acid ethyl ester, (0.035 g, 0.146 mmol) and 4-fluorobenzylamine (0.11 g, 0.88 mmol) in anhydrous ethyl alcohol (5 ml) and N,N-dimethylformamide (2 ml) was heated under reflux for 18 h. The solvent was then evaporated in vacuo and the residue was partitioned between ethyl acetate and 0.1 N hydrochloric acid. The organic phase was washed with water and brine then dried over anhydrous sodium sulfate. Evaporation of the solvent and recrystallization of the resulting solid from ethanol gave 0.016 g (34% yield) of the title amide as white crystals. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 4.46 (4H, broad s, 2×CH2), 7.17 (2H, m, aromatics), 7.36 (2H, m, aromatics), 9.07 (1H, broad t, NH), 11.8–12.4 (2H, broad, OH and NH). MS (ESI+) m/z 319 [M+H+].

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was then evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and 0.1 N hydrochloric acid
  5. washThe organic phase was washed with water and brine
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. customEvaporation of the solvent and recrystallization of the resulting solid from ethanol

출처 및 근거

ORD 기록
ord-30747c6ecbf541e0b2b443300b9fb58d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07192948B2

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