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Cesium carbonate → 5-(((1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-yl)oxy)methyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine

HRID 77455
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HRID 77455 반응식
Cl[CH2:2][C:3]1[CH:4]=[N:5][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[N:27]1[C:35]2[C:30](=[CH:31][C:32]([OH:36])=[CH:33][CH:34]=2)[C:29]([C:37]([F:40])([F:39])[F:38])=[N:28]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[O:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[N:27]1[C:35]2[C:30](=[CH:31][C:32]([O:36][CH2:2][C:3]3[CH:4]=[N:5][C:6]([NH:9][C:10]4[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=4)=[N:7][CH:8]=3)=[CH:33][CH:34]=2)[C:29]([C:37]([F:40])([F:38])[F:39])=[N:28]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 866797391-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-olHCID 866797425-(chloromethyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine

생성물 1

HCID 866797415-(((1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-yl)oxy)methyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine수율 52%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 5-(chloromethyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine (0.04 g, 0.132 mmol) in DMF (2 mL), 1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-ol (0.045 g, 0.158 mmol) and Cs2CO3 (0.086 g, 0.263 mmol) were added. The reaction mixture was stirred at room temperature for 18 h, then diluted in EtOAc and washed sequentially with 10% NaOH and brine. The organic layer was dried over Na2SO4 and concentrated to afford 5-(((1-(tetrahydro-2H-pyran-2-yl)-3-(trifluoromethyl)-1H-indazol-5-yl)oxy)methyl)-N-(4-(trifluoromethoxy)phenyl)pyrimidin-2-amine (38 mg, 52%). LCMS: RT 2.33 min; 554.0 [M+H]+.

후처리

  1. washwashed sequentially with 10% NaOH and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b171477ebac8420c833fe88d8648d206
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08841301B2

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