Methanol → N-[(1S)-3-{6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}-1-methylpropyl]acetamide

HRID 1026288Notes

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:18]=[CH:17][C:16]([C:19]#[C:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1.CO>[Pd].C1COCC1>[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:18]=[CH:17][C:16]([CH2:19][CH2:20][C@@H:21]([NH:23][C:24](=[O:26])[CH3:25])[CH3:22])=[CH:15][CH:14]=4)[O:12][C:8]=3[CH:7]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

Under a hydrogen atmosphere, a mixture of N-[(1S)-3-{6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}-1-methylprop-2-yn-1-yl]acetamide (98.0 mg), 10% palladium/carbon (containing water (50%), 19.6 mg), methanol (5 mL) and THF (1 mL) was stirred at 50° C. for 4 hr. The catalyst was removed by filtration, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol) to give the title compound as yellow crystals (37.0 mg).

Workup

customThe catalyst was removed by filtration
concentrationthe obtained filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate/methanol)

Sources & evidence

ORD record: ord-98f8612c50ca43e7a744d04b02ff1160
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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