p-Toluenesulfonic acid monohydrate → N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide p-toluenesulfonate

HRID 1874396

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:17]=[C:18]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:19]=[CH:20][CH:21]=4)=[CH:11][N:10]3[CH:32]=2)=[O:5])[CH2:3][CH2:2]1.O.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40]([OH:43])(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(O)C.C(OCC)(=O)C>[C:34]1([CH3:44])[CH:35]=[CH:36][C:37]([S:40]([OH:43])(=[O:41])=[O:42])=[CH:38][CH:39]=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:17]=[C:18]([NH:22][C:23]([C:25]5[N:29]([CH3:30])[N:28]=[C:27]([CH3:31])[CH:26]=5)=[O:24])[CH:19]=[CH:20][CH:21]=4)=[CH:11][N:10]3[CH:32]=2)=[O:5])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[3-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1,3-dimethyl-1H-pyrazole-5-carboxamide (204 mg, 0.474 mmol) in ethanol (8 mL) was added a solution of p-toluenesulfonic acid monohydrate (94.7 mg, 0.498 mmol) in ethyl acetate (1.10 mL), and the mixture was stirred at 0° C. for 2 hr and at room temperature for 2 days. The precipitated solid was collected by filtration and washed with ethanol to give the title compound (192 mg, 67%) as a white solid.

Workup

filtrationThe precipitated solid was collected by filtration
washwashed with ethanol

Sources & evidence

ORD record: ord-03a8fbf0bfba4b0bb725282d08c13a5b
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304557B2

Linked notes

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