(1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-(3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl)-3-((1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)urea

HRID 1843000ノート

反応式

HRID 1843000 の反応式
Cl.[C:2]1([CH3:19])[CH:7]=[CH:6][CH:5]=[C:4]([N:8]2[C:12]([CH2:13][NH2:14])=[CH:11][C:10]([C:15]([F:18])([F:17])[F:16])=[N:9]2)[CH:3]=1.[F:20][C:21]1[CH:22]=[C:23]([NH:32][C:33](=O)[O:34]C2C=CC=CC=2)[CH:24]=[CH:25][C:26]=1[N:27]1[CH2:30][CH:29]([OH:31])[CH2:28]1>C(#N)C>[F:20][C:21]1[CH:22]=[C:23]([NH:32][C:33]([NH:14][CH2:13][C:12]2[N:8]([C:4]3[CH:3]=[C:2]([CH3:19])[CH:7]=[CH:6][CH:5]=3)[N:9]=[C:10]([C:15]([F:17])([F:16])[F:18])[CH:11]=2)=[O:34])[CH:24]=[CH:25][C:26]=1[N:27]1[CH2:30][CH:29]([OH:31])[CH2:28]1

参加物

4

反応物 2

HCID 70816262(1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672171Phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate

生成物 1

HCID 708162831-(3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl)-3-((1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)urea収率 71%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of (1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (75 mg, 0.257 mmol, 1.0 eq) in acetonitrile (6 mL) was added TEA (0.14 mL, 1.0 mmol, 4.0 eq) followed by phenyl 3-fluoro-4-(3-hydroxyazetidin-1-yl)phenylcarbamate (78 mg, 0.262 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 (4:1) as eluent) to get 1-(3-fluoro-4-(3-hydroxyazetidin-1-yl)phenyl)-3-((1-m-tolyl-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)urea (71 mg, 71%).

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 (4:1) as eluent)

出典と根拠

ORDレコード
ord-dc3caf0058e0407e813a2ccd347c4845
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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