Hydrochloric Acid → HCID 66969144, compound

HRID 2095951Notes

Reaction equation

HRID 2095951 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)[N:28]([CH3:31])[C:29]=5[CH3:30])=[O:24])=[CH:18][C:17]=4[F:40])=[CH:11][N:10]3[CH:41]=2)=[O:5])[CH2:3][CH2:2]1.[ClH:42]>C(C(C)=O)C.O>[OH2:5].[ClH:42].[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:33]=[CH:34][C:35]([F:38])=[CH:36][CH:37]=6)[N:28]([CH3:31])[C:29]=5[CH3:30])=[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58158588HCID 58158588, compound

Product 1

HCID 66969144HCID 66969144, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a suspension of N-[4-({2-[(cyclopropylcarbonyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)-3-fluorophenyl]-2-(4-fluorophenyl)-1,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxamide (400 mg, 0.72 mmol) in methyl ethyl ketone (7 mL) and water (5 mL) was slowly added 6N aqueous hydrochloric acid solution (240 μL), and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration, washed with methyl ethyl ketone and suspended in ethanol (5 mL), and the suspension was stirred at 70° C. for 10 min. The solid was collected by filtration, washed with ethanol and dried under reduced pressure to give the title compound (120 mg, 27%) as a white solid.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with methyl ethyl ketone
  3. stirringthe suspension was stirred at 70° C. for 10 min
  4. filtrationThe solid was collected by filtration
  5. washwashed with ethanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-52105e30b5604907bc74fde16ee0a384
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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