Ethanamine, 2,2,2-trifluoro- → 6-chloro-4-(4-fluorophenyl)-4-hydroxy-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 19681

反応式

HRID 19681 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](N2C=CN=C2)=[O:10])=[C:4]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:3]=1.[F:25][C:26]([F:30])([F:29])[CH2:27][NH2:28]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:8][C:9](=[O:10])[N:28]([CH2:27][C:26]([F:30])([F:29])[F:25])[C:16]2([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[OH:24]

参加物

4

反応物 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 59346602N-(4-chloro-2-(4-fluorobenzoyl)phenyl)-1H-imidazole-1-carboxamide

生成物 1

HCID 593465986-chloro-4-(4-fluorophenyl)-4-hydroxy-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a suspension of N-[4-chloro-2-(4-fluorobenzoyl)phenyl]-1H-imidazole-1-carboxamide (63.0 g, 183.3 mmol) in THF (315 mL) was added 2,2,2-trifluoroethylamine (24.5 g, 247.4 mmol). The reaction was heated to 50° C. After 19 h at 50° C., the reaction was cooled to ambient temperature and concentrated in vacuo. The light yellow oil was partitioned between n-butyl chloride (110 mL) and aqueous 10% citric acid (60 mL) with vigorous stirring. The resulting precipitate was collected by vacuum filtration and placed under vacuum alongside P2O5 for 16 h to give 6-chloro-4-(4-fluorophenyl)-4-hydroxy-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinazolin-2(1H)-one as an off-white solid.

後処理

  1. temperaturethe reaction was cooled to ambient temperature
  2. concentrationconcentrated in vacuo
  3. customThe light yellow oil was partitioned between n-butyl chloride (110 mL) and aqueous 10% citric acid (60 mL) with vigorous stirring
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. waitplaced under vacuum alongside P2O5 for 16 h

出典と根拠

ORDレコード
ord-682f636ab7e642f095db80e1eed6da3e
出典データセット
uspto-grants-2010_06
特許番号
US07745452B2

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