Potassium Carbonate → 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]methoxy}pyridin-2(1H)-one

HRID 1497413노트

반응식

HRID 1497413 반응식
[CH:1]1([N:4]2[C:12]([CH3:13])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])=[CH:10]3)=[N:5]2)[CH2:3][CH2:2]1.Cl[CH2:23][C:24]1[N:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[S:27][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH:1]1([N:4]2[C:12]([CH3:13])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([N:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:23][C:24]5[N:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[S:27][CH:28]=5)=[CH:16][C:15]4=[O:21])=[CH:10]3)=[N:5]2)[CH2:2][CH2:3]1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 177504144-(Chloromethyl)-2-(trifluoromethyl)-1,3-thiazoleHCID 1177986831-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

생성물 1

HCID 904694381-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-{[2-(trifluoromethyl)-1,3-thiazol-4-yl]methoxy}pyridin-2(1H)-one수율 44.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (200 mg) and 4-(chloromethyl)-2-(trifluoromethyl)thiazole (172 mg) in DMF (4 ml) was added potassium carbonate (118 mg) at room temperature, and the mixture was stirred at the same temperature overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was fractionated by HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% NH4HCO3)), and saturated aqueous sodium hydrogen carbonate solution was added to the obtained fraction. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from methanol-water to give the title compound (141 mg).

후처리

  1. washwashed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionwas added to the obtained fraction
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol-water

출처 및 근거

ORD 기록
ord-9a3b0c4086274e19a9af5b3372ec03dd
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199963B2

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