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Potassium Carbonate → 5-Chloro-4-(5-chloro-6-(3,3-difluoroazetidin-1-yl)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide

HRID 2048025
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인쇄 미리보기

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HRID 2048025 반응식
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.[Cl:8][C:9]1[C:10]([O:23][C:24]2[CH:25]=[N:26][C:27](F)=[C:28]([Cl:30])[CH:29]=2)=[CH:11][C:12]([F:22])=[C:13]([CH:21]=1)[C:14]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[Cl:8][C:9]1[C:10]([O:23][C:24]2[CH:25]=[N:26][C:27]([N:5]3[CH2:6][C:3]([F:7])([F:2])[CH2:4]3)=[C:28]([Cl:30])[CH:29]=2)=[CH:11][C:12]([F:22])=[C:13]([CH:21]=1)[C:14]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[O:15]
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6

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HCID 11430Potassium CarbonateHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 580424375-Chloro-4-[(5-chloro-6-fluoropyridin-3-yl)oxy]-2-fluoro-N-(methylsulfonyl)benzamide

생성물 1

HCID 580423595-Chloro-4-(5-chloro-6-(3,3-difluoroazetidin-1-yl)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide수율 25%

시약·촉매·용매 2

HCID 679
Dimethyl Sulfoxide
용매
HCID 962Water용매

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온도
90 °C

실험 절차

3,3-Difluoroazetidine hydrochloride (98 mg, 0.76 mmol) was added to a suspension of 5-chloro-4-(5-chloro-6-fluoropyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide (Example 19, 150 mg, 0.38 mmol) and potassium carbonate (74 mg, 0.53 mmol) in dimethylsulfoxide (1 mL). The reaction mixture was stirred at 90° C. in the microwave for 15 hours. The reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude compound was purified by reverse phase preparative HPLC eluting with acetonitrile:water (from 5:95 to 95:5) to give the title compound as a colourless solid (44 mg, 25%).

후처리

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by reverse phase preparative HPLC
  6. washeluting with acetonitrile

출처 및 근거

ORD 기록
ord-153c05bd946446469fa10c2e50398876
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592629B2

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