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 2277321ノート

反応式

HRID 2277321 の反応式
[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]

参加物

6

反応物 4

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

生成物 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)acetamide収率 82.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-10c39d9908124f549b827ba05b75564a
出典データセット
uspto-grants-2015_09
特許番号
US09133129B2

反応ノート

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