4,4,4-Trifluoro-1-phenyl-1,3-butanedione → 2-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol

HRID 891063

反応式

HRID 891063 の反応式
Cl.[NH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1)[NH2:3].[C:13]([CH2:21][C:22](=O)[C:23]([F:26])([F:25])[F:24])(=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[C:14]1([C:13]2[N:2]([C:4]3[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][OH:12])=[CH:8][CH:9]=3)[N:3]=[C:22]([C:23]([F:24])([F:25])[F:26])[CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

4

反応物 2

HCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 222447112-(4-Hydrazinophenyl)ethanol hydrochloride

生成物 1

HCID 222445582-{4-[5-Phenyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]phenyl}ethanol収率 56.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 2-(4-hydrazinophenyl)ethanol hydrochloride (J. Med. Chem., 1999, 42, 2504, 202 mg, 1.07 mmol) and benzoyl-1,1,1-trifluoroacetone (278 mg, 1.28 mmol) in ethanol (13 mL) was heated under reflux overnight. After removal of the solvent, the resulting residue was partitioned between dichloromethane and water. Organic phase was washed with brine and dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 200 mg (56%) of the title compound as yellow solids: MS (ESI) m/z 333 [M+H]+, 1H-NMR (CDCl3) δ 7.36-7.20 (9H, m), 6.74 (1H, s), 3.86 (2H, br.s), 2.89 (2H, t, J=6.6 Hz).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customAfter removal of the solvent
  4. customthe resulting residue was partitioned between dichloromethane and water
  5. washOrganic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. customAfter removal of the solvent
  8. customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-9e07c64372314e6692139765531f2263
出典データセット
uspto-grants-2006_02
特許番号
US07001917B2

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