Potassium Hydroxide → N-(3-fluoro-4-(7-((1-hydroxycyclopropyl)methoxy)quinolin-4-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 1517876Notes

Reaction equation

HRID 1517876 reaction equation
C([O:4][C:5]1([CH2:8][O:9][C:10]2[CH:19]=[C:18]3[C:13]([C:14]([O:20][C:21]4[CH:26]=[CH:25][C:24]([NH:27][C:28]([C:30]5[C:31](=[O:43])[N:32]([C:37]6[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=6)[N:33]([CH3:36])[C:34]=5[CH3:35])=[O:29])=[CH:23][C:22]=4[F:44])=[CH:15][CH:16]=[N:17]3)=[CH:12][CH:11]=2)[CH2:7][CH2:6]1)(=O)C.[OH-].[K+]>CO>[F:44][C:22]1[CH:23]=[C:24]([NH:27][C:28]([C:30]2[C:31](=[O:43])[N:32]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:33]([CH3:36])[C:34]=2[CH3:35])=[O:29])[CH:25]=[CH:26][C:21]=1[O:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([O:9][CH2:8][C:5]3([OH:4])[CH2:6][CH2:7]3)=[CH:11][CH:12]=2)[N:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66684940HCID 66684940, compound

Product 1

HCID 66670625N-(3-fluoro-4-(7-((1-hydroxycyclopropyl)methoxy)quinolin-4-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compounds 1-((4-(4-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)-2-fluorophenoxy)quinolin-7-yloxy)methyl)cyclopropyl acetate (110 mg, 0.18 mmol) in 8 mL of methanol was added KOH (100 mg, 1.78 mmol) slowly. After stirring at rt for 0.5 hr, the reaction mixture was filtered and the solid was washed with ethyl acetate (10 mL×2) to give the title compound as a white solid (100 mg, 29%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe solid was washed with ethyl acetate (10 mL×2)

Sources & evidence

ORD record
ord-00fd4e165355417eae1104d3a58a8bba
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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