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

HRID 891063노트

반응식

HRID 891063 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9e07c64372314e6692139765531f2263
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001917B2

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