Ethanol → N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 1874392

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[CH:19][C:20]4[N:21]([CH:23]=[C:24]([NH:26]C(=O)C(F)(F)F)[N:25]=4)[CH:22]=3)[CH:11]=2)=[O:8])=[CH:5][C:4]([CH3:33])=[N:3]1.[OH-].[Na+].C(O)C>O>[NH2:26][C:24]1[N:25]=[C:20]2[CH:19]=[CH:18][C:17]([O:16][C:12]3[CH:11]=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:33])[CH:5]=4)=[O:8])[CH:15]=[CH:14][CH:13]=3)=[CH:22][N:21]2[CH:23]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 1,3-dimethyl-N-[3-({2-[(trifluoroacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1H-pyrazole-5-carboxamide (328 mg, 0.715 mmol), 1N aqueous sodium hydroxide solution (3 mL) and ethanol (3 mL) was stirred at 40° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80) to give the title compound (205 mg, 79%) as a white solid.

Workup

extractionextracted with ethyl acetate (×3)
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by column chromatography (silica gel, methanol/ethyl acetate=0/100→20/80)

Sources & evidence

ORD record: ord-e8d24731029c4ab69d016190cc4b6390
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Linked notes

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