(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea

HRID 1842915노트

반응식

HRID 1842915 반응식
[OH:1][C:2]1([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:21])OC3C=CC=CC=3)=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.Cl.[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH2:36])=[CH:33][C:32]([C:37]([F:40])([F:39])[F:38])=[N:31]2)[CH:27]=[CH:28][CH:29]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:25]=[C:26]([N:30]2[C:34]([CH2:35][NH:36][C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([C:2]4([OH:1])[CH2:3][O:4][CH2:5]4)=[CH:11][CH:10]=3)=[O:21])=[CH:33][C:32]([C:37]([F:38])([F:39])[F:40])=[N:31]2)[CH:27]=[CH:28][CH:29]=1

참가 물질

4

반응물 2

HCID 70816151(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochlorideHCID 86672148Phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate

생성물 1

HCID 708161031-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea수율 61.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

To a stirred solution of phenyl 4-(3-hydroxyoxetan-3-yl)phenylcarbamate (100 mg, 0.35 mmol, 1.0 eq) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (119.3 mg, 0.35 mmol, 1.0 eq) in DCM (10 mL) was added TEA (106 mg, 1.049 mmol, 3.0 eq) at RT and stirred at 40° C. overnight. The mixture was diluted with DCM (30 mL) and washed with water (10 mL), brine (10 mL) and dried over anhydrous Na2SO4 and concentrated. Crude product was purified by CC using MeOH/CHCl3 (1:9) to get 1-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)-3-(4-(3-hydroxyoxetan-3-yl)phenyl)urea (100 mg; 61%) as a white solid (TLC system: MeOH/CHCl3 (1:9); Rf: 0.45).

후처리

  1. washwashed with water (10 mL), brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customCrude product was purified by CC

출처 및 근거

ORD 기록
ord-63c6e07def374b28a22cb2f2aad6ed57
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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