Sodium Hydroxide → N-(5-((2-(3-hydroxycyclobutanecarboxamido)pyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 520710Notes

Reaction equation

HRID 520710 reaction equation
C([O:4][CH:5]1[CH2:8][CH:7]([C:9](=[O:41])[NH:10][C:11]2[CH:16]=[C:15]([O:17][C:18]3[CH:19]=[N:20][C:21]([NH:24][C:25]([C:27]4[C:28](=[O:40])[N:29]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[N:30]([CH3:33])[C:31]=4[CH3:32])=[O:26])=[CH:22][CH:23]=3)[CH:14]=[CH:13][N:12]=2)[CH2:6]1)(=O)C.[OH-].[Na+]>CO>[OH:4][CH:5]1[CH2:6][CH:7]([C:9]([NH:10][C:11]2[CH:16]=[C:15]([O:17][C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]4[C:28](=[O:40])[N:29]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[N:30]([CH3:33])[C:31]=4[CH3:32])=[O:26])=[N:20][CH:19]=3)[CH:14]=[CH:13][N:12]=2)=[O:41])[CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 900336043-((4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutyl acetate

Product 1

HCID 73051379N-(5-((2-(3-hydroxycyclobutanecarboxamido)pyridin-4-yl)oxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 45.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-((4-((6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamido)pyridin-3-yl)oxy)pyridin-2-yl)carbamoyl)cyclobutyl acetate (40 mg, 0.072 mmol) in MeOH (2.5 mL) was cooled to 0° C., then NaOH (6 mg, 0.144 mmol) was added to the mixture. The reaction was stirred at rt for 1 hour, then concentrated in vacuo. The residue was washed with water (5 mL) and ether (5 mL), then filtered to give the title compound as a white solid (17 mg, 42%).

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed with water (5 mL) and ether (5 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-694d1419724242eca1b2b502cbf134c5
Source dataset
uspto-grants-2016_05
Patent number
US09326975B2

Reaction notes

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