Acetonitrile → N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-4-fluoro-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide

HRID 1026226Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])[CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.[B-](F)(F)(F)[F:30].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(#N)C>O>[CH:1]1([CH2:4][O:5][C:6]2[CH:28]=[CH:27][C:9]3[N:10]=[C:11]([C:13]4[N:17]([CH3:18])[N:16]=[C:15]([O:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])[C:14]=4[F:30])[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-[(1S)-2-({5-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-1-methyl-1H-pyrazol-3-yl}oxy)-1-methylethyl]acetamide (193 mg), 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane ditetrafluoroborate (427 mg) and acetonitrile (10 mL) was stirred at 60° C. for 7 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (11.2 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-116e4b2c2b0a45afadb1b95ed29c0fae
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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