p-Toluenesulfonic acid monohydrate → HCID 86651403, compound

HRID 2095966Notes

Reaction equation

HRID 2095966 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[N+:26]([O-:39])=[C:27]([C:32]6[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[CH:18][C:17]=4[F:40])=[CH:11][N:10]3[CH:41]=2)=[O:5])[CH2:3][CH2:2]1.O.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>C(O)C>[C:43]1([CH3:53])[CH:44]=[CH:45][C:46]([S:49]([OH:52])(=[O:50])=[O:51])=[CH:47][CH:48]=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[N+:26]([O-:39])=[C:27]([C:32]6[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[CH:33]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[CH:18][C:17]=4[F:40])=[CH:11][N:10]3[CH:41]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58158543HCID 58158543, compound

Product 1

HCID 86651403HCID 86651403, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

An ethanol (20 mL) suspension containing N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-6-(3-fluorophenyl)-5-methylpyridine-2-carboxamide 1-oxide (833 mg, 1.50 mmol) was heated to 90° C., and p-toluenesulfonic acid monohydrate (314 mg, 1.65 mmol) was added. When the mixture became a uniform transparent solution, the precipitated solid was collected by filtration and washed with ethanol to give the title compound (870 mg, 80%) as a white solid.

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washwashed with ethanol

Sources & evidence

ORD record
ord-7797d9dc095d4478b55fb57a67fbcad7
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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