Hydrochloric Acid → N-[6-(4-amino-3-fluorophenoxy)imidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095767Notes

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)=[C:18]([F:33])[CH:17]=4)=[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)=[CH:17][C:18]=1[F:33]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of benzyl [4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]carbamate (9.7 g, 21.1 mmol) in 1,2-dimethoxyethane (291 mL) was added 0.15 mol/L aqueous barium hydroxide solution (194 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 extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous sodium 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 (4.3 g, 63%).

Workup

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

Sources & evidence

ORD record: ord-5c5cea062a504183a2ddbd12b7b7996f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

Loading…