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 2277321Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-10c39d9908124f549b827ba05b75564a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133129B2

Reaction notes

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