Dimethylformamide → N-((2S)-1-((2-(4-(2-(2,2-difluorocyclopropyl)ethoxy)-3-fluorophenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

HRID 2277321노트

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HRID 2277321 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:10][C:11]3[CH:16]=[C:15]([O:17][CH2:18][C@@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])[N:14]=[CH:13][C:12]=3[N:25]=2)[CH:5]=[CH:6][C:7]=1[OH:8].CS(O[CH2:31][CH2:32][CH:33]1[CH2:35][C:34]1([F:37])[F:36])(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:36][C:34]1([F:37])[CH2:35][CH:33]1[CH2:32][CH2:31][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[O:10][C:11]3[CH:16]=[C:15]([O:17][CH2:18][C@@H:19]([NH:21][C:22](=[O:24])[CH3:23])[CH3:20])[N:14]=[CH:13][C:12]=3[N:25]=2)=[CH:3][C:2]=1[F:1]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 866663152-(2,2-Difluorocyclopropyl)ethyl methanesulfonateHCID 136341410HCID 136341410, 화합물

생성물 1

HCID 86731409N-((2S)-1-((2-(4-(2-(2,2-difluorocyclopropyl)ethoxy)-3-fluorophenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide수율 82.2%

시약·촉매·용매 1

HCID 962Water용매

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온도
70 °C

실험 절차

A mixture of N-((2S)-1-((2-(3-fluoro-4-hydroxyphenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide (100 mg), 2-(2,2-difluorocyclopropyl)ethyl methanesulfonate (232 mg), potassium carbonate (160 mg) and DMF (1 mL) was stirred overnight at 70° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized (ethyl acetate) to give the title compound (107 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized (ethyl acetate)

출처 및 근거

ORD 기록
ord-10c39d9908124f549b827ba05b75564a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133129B2

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