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

HRID 458694ノート

反応式

HRID 458694 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-30747c6ecbf541e0b2b443300b9fb58d
出典データセット
uspto-grants-2007_03
特許番号
US07192948B2

反応ノート

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