Hydrochloric Acid → N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide hydrochloride

HRID 2277378Notes

Reaction equation

HRID 2277378 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26]([C:28]2[C:29](=[O:41])[N:30]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:31]([CH3:34])[C:32]=2[CH3:33])=[O:27])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.[ClH:42]>C(Cl)Cl.CO.CCOC(C)=O>[ClH:42].[F:1][C:2]1[CH:3]=[C:4]([NH:25][C:26]([C:28]2[C:29](=[O:41])[N:30]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:31]([CH3:34])[C:32]=2[CH3:33])=[O:27])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:20][C:21]([OH:24])([CH3:23])[CH3:22])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60165029Ningetinib

Product 1

HCID 68193815N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide hydrochlorideYield 95.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of N-(3-fluoro-4-((7-(2-hydroxy-2-methylpropoxy)quinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (300 mg, 0.54 mmol) in DCM/MeOH (30 mL, v/v=1:2) was added 1 N HCl in EtOAc (5.4 mL). The mixture was stirred at room temperature for 30 minutes. The solid was collected by filtration, washed with ethanol (20 mL) to give the title compound as a white solid (304 mg, 95.2%)

Workup

  1. filtrationThe solid was collected by filtration
  2. washwashed with ethanol (20 mL)

Sources & evidence

ORD record
ord-0cfbd4a643544dedb62ecdbb89f1ffad
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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