Hydrochloric Acid → N-[6-(4-amino-2-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095760Notes

Reaction equation

[CH:1]1([C:4]([NH:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([NH:22]C(=O)OCC5C=CC=CC=5)=[CH:18][C:17]=4[F:33])=[CH:11][N:10]3[CH:34]=2)=[O:5])[CH2:3][CH2:2]1.[OH-].[Ba+2].[OH-].Cl>COCCOC>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:12]2[CH:13]=[CH:14][C:9]3[N:10]([CH:34]=[C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])[N:8]=3)[CH:11]=2)=[C:17]([F:33])[CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]carbamate (18.0 g, 39.1 mmol) in 1,2-dimethoxyethane (360 mL) was added 0.15 mol/L aqueous barium hydroxide solution (240 mL), and the mixture was stirred at 90° C. for 16 hr. After cooling to room temperature, the reaction mixture was adjusted to about pH 8 with 2N hydrochloric acid, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate and collected by filtration to give the title compound (9.1 g, 71%).

Workup

temperatureAfter cooling to room temperature
extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
washthe residue was washed with ethyl acetate
filtrationcollected by filtration

Sources & evidence

ORD record: ord-c60928f70e9c4b0cb9e45eb2e6756181
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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