Diethyl Ether → 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 methanesulfonate

HRID 2095961Notes

Reaction equation

HRID 2095961 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:23]([C:25]5[C:26](=[O:38])[N:27]([C:32]6[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[CH:18][C:17]=4[F:39])=[CH:11][N:10]3[CH:40]=2)=[O:5])[CH2:3][CH2:2]1.[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].C(OCC)C>C(O)C>[CH3:41][S:42]([OH:45])(=[O:44])=[O:43].[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:23]([C:25]5[C:26](=[O:38])[N:27]([C:32]6[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[CH:18][C:17]=4[F:39])=[CH:11][N:10]3[CH:40]=2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 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 86651402N-[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 methanesulfonateYield 93.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension (3 mL) of 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) in ethanol was heated to 80° C., and a solution (1 mL) of methanesulfonic acid (107 mg, 1.12 mmol) in ethanol was added. The mixture was cooled to room temperature, diethyl ether was added dropwise, and the obtained solid was collected by filtration to give the title compound (550 mg, 93%) as a white solid.

Workup

  1. filtrationthe obtained solid was collected by filtration

Sources & evidence

ORD record
ord-37ff2842c54446c195cf0e6a28256a2f
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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