p-Toluenesulfonic acid monohydrate → 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 p-toluenesulfonate

HRID 2095959Notes

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.O.[C:42]1([CH3:52])[CH:47]=[CH:46][C:45]([S:48]([OH:51])(=[O:50])=[O:49])=[CH:44][CH:43]=1>C(O)C>[C:42]1([CH3:52])[CH:43]=[CH:44][C:45]([S:48]([OH:51])(=[O:49])=[O:50])=[CH:46][CH:47]=1.[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

Conditions

Temperature: 70 °C

Procedure

To a suspension 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 (650 mg, 1.21 mmol) in ethanol (6.5 ml) was added p-toluenesulfonic acid monohydrate (276 mg, 1.45 mmol) at 70° C. The reaction solution was stirred at 70° C. for 1 hr, and the precipitate was collected by filtration and washed with ethanol to give the title compound (702 mg, 82%) as white crystals.

Workup

filtrationthe precipitate was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-d59e39f44c83405c841ad2100824f66f
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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