p-Toluenesulfonic acid monohydrate → N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide p-toluenesulfonate

HRID 2095958Notes

Reaction equation

HRID 2095958 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:39])[N:27]([C:32]6[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[C:18]([F:40])[CH:17]=4)=[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>O1CCCC1>[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[C:26](=[O:39])[N:27]([C:32]6[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[C:18]([F:40])[CH:17]=4)=[CH:11][N:10]3[CH:41]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58158452N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 86651400N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide p-toluenesulfonateYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-2-fluorophenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide (300 mg, 0.54 mmol) was added tetrahydrofuran (15 mL), and the mixture was dissolved by heating at 60° C. p-Toluenesulfonic acid monohydrate (123.3 mg, 0.65 mmol) was added. The mixture was stirred at 50° C. for 1 hr and at 40° C. for 12 hr. After cooling to room temperature, the precipitate was collected by filtration, washed with tetrahydrofuran and dried at 100° C. for 3 hr under reduced pressure to give the title compound (259 mg, 66%) as a white powder.

Workup

  1. dissolutionthe mixture was dissolved
  2. additionwas added
  3. temperatureAfter cooling to room temperature
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with tetrahydrofuran
  6. customdried at 100° C. for 3 hr under reduced pressure

Sources & evidence

ORD record
ord-9195aae5612a4bb3881278c6f17010f3
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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