(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 1843000노트

반응식

HRID 1843000 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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%).

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 (4:1) as eluent)

출처 및 근거

ORD 기록
ord-dc3caf0058e0407e813a2ccd347c4845
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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