Ethanol → HCID 24767982, compound

HRID 1663698Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:19]=[C:20]([NH:24][C:25](=[O:36])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=5)[CH:21]=[CH:22][CH:23]=4)=[N:13][N:12]3[CH:37]=2)[CH:5]=[CH:4][N:3]=1.[CH3:38][NH2:39].O1CCCC1.C(O)C>C(OCC)(=O)C>[CH3:38][NH:39][C:2]1[N:7]=[C:6]([NH:8][C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:19]=[C:20]([NH:24][C:25](=[O:36])[C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:35])[F:33])[CH:27]=5)[CH:21]=[CH:22][CH:23]=4)=[N:13][N:12]3[CH:37]=2)[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of N-[3-({2-[(2-chloropyrimidin-4-yl)amino]imidazo[1,2-b]pyridazin-6-yl}oxy)phenyl]-3-(trifluoromethyl)benzamide (122 mg, 0.23 mmol), 2M methylamine-tetrahydrofuran solution (3.0 mL) and ethanol (6.0 mL) was heated to 70° C., and the mixture was stirred overnight. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtrated, and the residue was purified by silica gel column chromatography (ethyl acetate alone→ethyl acetate/methanol=4:1). The obtained residue was washed with ethyl acetate-hexane to give the title compound (60 mg, 50%) as a yellow solid.

Workup

washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltrated
customthe residue was purified by silica gel column chromatography (ethyl acetate alone→ethyl acetate/methanol=4:1)
washThe obtained residue was washed with ethyl acetate-hexane

Sources & evidence

ORD record: ord-4d18369f4a5a4fdeaa74174dad2f6475
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08034812B2

Reaction notes

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