(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 1842950ノート

反応式

HRID 1842950 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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))

出典と根拠

ORDレコード
ord-dcad5138a4824165b88bb716fc6b7f0e
出典データセット
uspto-grants-2015_02
特許番号
US08946204B2

反応ノート

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