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

HRID 2095956Notes

Reaction equation

HRID 2095956 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])=[CH:18][CH:17]=4)=[CH:11][N:10]3[CH:40]=2)=[O:5])[CH2:3][CH2:2]1.O.[C:42]1([S:48]([OH:51])(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1>[OH2:5].[C:42]1([S:48]([OH:51])(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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]=[CH:18][C:19]([NH:22][C:23]([C:25]5[C:26](=[O:39])[N:27]([C:32]6[CH:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=6)[C:28]([CH3:31])=[CH:29][CH:30]=5)=[O:24])=[CH:20][CH:21]=4)=[CH:11][N:10]3[CH:40]=2)=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 15619088Hydroxybenzenesulfonic acidHCID 58158601N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 86651399N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide benzenesulfonate monohydrateYield 116.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (90 mL) of N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]-1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide (400 mg, 0.744 mmol) in tetrahydrofuran was added benzenesulfonic acid monohydrate (197 mg, 1.12 mmol) at 80° C. The mixture was filtered, and the filtrate was gradually cooled to room temperature. The solution at room temperature was distilled off at 110° C. to evaporate tetrahydrofuran to about half, and gradually cooled again to room temperature. The precipitate was collected by filtration, and the solid was washed with tetrahydrofuran and dried to give the title compound (309 mg, 58%) as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. distillationThe solution at room temperature was distilled off at 110° C.
  3. customto evaporate tetrahydrofuran to about half
  4. temperaturegradually cooled again to room temperature
  5. filtrationThe precipitate was collected by filtration
  6. washthe solid was washed with tetrahydrofuran
  7. customdried

Sources & evidence

ORD record
ord-ebd856d1ad914cbd841d75b7380886bd
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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