(1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-((1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-((2-hydroxyethoxy)methyl)phenyl)urea

HRID 1842950노트

반응식

HRID 1842950 반응식
Cl.[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([N:12]2[C:16]([CH2:17][NH2:18])=[CH:15][C:14]([C:19]([F:22])([F:21])[F:20])=[N:13]2)[CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH3:3].[F:23][C:24]1[CH:25]=[C:26]([NH:35][C:36](=O)[O:37]C2C=CC=CC=2)[CH:27]=[CH:28][C:29]=1[CH2:30][O:31][CH2:32][CH2:33][OH:34]>C(#N)C>[CH2:2]([O:4][C:5]1[CH:6]=[C:7]([N:12]2[C:16]([CH2:17][NH:18][C:36]([NH:35][C:26]3[CH:27]=[CH:28][C:29]([CH2:30][O:31][CH2:32][CH2:33][OH:34])=[C:24]([F:23])[CH:25]=3)=[O:37])=[CH:15][C:14]([C:19]([F:20])([F:21])[F:22])=[N:13]2)[CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH3:3]

참가 물질

4

반응물 2

HCID 70816994(1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672156Phenyl 3-fluoro-4-((2-hydroxyethoxy)methyl)-phenylcarbamate

생성물 1

HCID 708162481-((1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-((2-hydroxyethoxy)methyl)phenyl)urea수율 39.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirred solution of (1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (100 mg, 0.300 mmol, 1.0 eq) in acetonitrile (7 mL) was added TEA (0.166 mL, 1.20 mmol, 4.0 eq) followed by phenyl 3-fluoro-4-((2-hydroxyethoxy)methyl)-phenylcarbamate (93 mg, 0.306 mmol, 1.02 eq) and stirred at reflux for 16 h. The solvent of the reaction mixture was evaporated and the residue was purified by column chromatography (EtOAc/cyclohexane (1:1)) to get 1-((1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(3-fluoro-4-((2-hydroxyethoxy)methyl)phenyl)urea (60 mg, 39%).

후처리

  1. temperatureat reflux for 16 h
  2. customThe solvent of the reaction mixture was evaporated
  3. customthe residue was purified by column chromatography (EtOAc/cyclohexane (1:1))

출처 및 근거

ORD 기록
ord-dcad5138a4824165b88bb716fc6b7f0e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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