Potassium Carbonate → (2R,3R)-2-(2,4-difluorophenyl)-3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

HRID 1430085노트

반응식

HRID 1430085 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1.CC(C)([O-])C.[K+].[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C@@:28]1([CH2:32][N:33]2[CH:37]=[N:36][CH:35]=[N:34]2)[C@@H:30]([CH3:31])[O:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C@:28]([OH:29])([C@H:30]([O:13][CH:10]1[CH2:9][CH2:8][N:7]([C:2]2[N:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:12][CH2:11]1)[CH3:31])[CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 107058781-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazoleHCID 202340981-(Pyrimidin-2-yl)piperidin-4-olHCID 23665647Potassium tert-butoxide

생성물 1

HCID 67367867(2R,3R)-2-(2,4-difluorophenyl)-3-((1-(pyrimidin-2-yl)piperidin-4-yl)oxy)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol수율 21%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-(pyrimidin-2-yl)piperidin-4-ol (19.4 mg, 0.08 mmol) in N,N-dimethylformamide (0.5 mL) was added potassium tert-butoxide (10.7 mg, 0.01 mmol), followed by stirring at room temperature for 2 hrs. The resulting solution was mixed with 1-(((2R,3R)-2-(2,4-difluorophenyl)-3-methyloxiran-2-yl)methyl)-1H-1,2,4-triazole (20.0 mg, 0.08 mmol) and anhydrous potassium carbonate (13.2 mg, 0.01 mmol) and stirred at room temperature for one hr. The resulting reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous ammonium chloride solution and then with saline to separate an organic solvent layer. The organic solvent layer was dried over anhydrous magnesium sulfate and concentrated by evaporation at reduced pressure. The concentrate was purified using silica gel chromatography to afford the title compound (yield 21%).

후처리

  1. stirringstirred at room temperature for one hr
  2. customThe resulting reaction mixture
  3. washwashed with a saturated aqueous ammonium chloride solution
  4. customwith saline to separate an organic solvent layer
  5. dry with materialThe organic solvent layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation at reduced pressure
  7. customThe concentrate was purified

출처 및 근거

ORD 기록
ord-709f1cc0cd4f4cf186592b32e877c7c6
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940768B2

반응 노트

불러오는 중…