Hydrochloride methanol → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 2095960Notes

Reaction equation

[ClH:1].CO.[CH:4]1([C:7]([NH:9][C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]5[C:29](=[O:41])[N:30]([C:35]6[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=6)[C:31]([CH3:34])=[CH:32][CH:33]=5)=[O:27])=[CH:21][C:20]=4[F:42])=[CH:14][N:13]3[CH:43]=2)=[O:8])[CH2:6][CH2:5]1>>[ClH:1].[CH:4]1([C:7]([NH:9][C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([O:18][C:19]4[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]5[C:29](=[O:41])[N:30]([C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=6)[C:31]([CH3:34])=[CH:32][CH:33]=5)=[O:27])=[CH:21][C:20]=4[F:42])=[CH:14][N:13]3[CH:43]=2)=[O:8])[CH2:6][CH2:5]1

Participants

Reactant 2

HCID 21893726Hydrochloride methanol

HCID 44595039N-(4-((2-((cyclopropylcarbonyl)amino)imidazo(1,2-a)pyridin-6-yl)oxy)-3-fluorophenyl)-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 66968886N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 79%

Procedure

A solution (5 to 10%) of hydrogen chloride/methanol was heated to 50° C., and N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-6-methyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxamide (500 mg, 0.93 mmol) was added. The mixture was stirred for 5 min and at room temperature for 30 min. The precipitate was collected by filtration and washed with methanol to give the title compound (420 mg, 79%) as white crystals.

Workup

filtrationThe precipitate was collected by filtration
washwashed with methanol

Sources & evidence

ORD record: ord-f8c0be460739408cbb5e57dbdb4a8ea5
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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