Potassium Carbonate → HCID 60172850, compound

HRID 2277408Notes

Reaction equation

HRID 2277408 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]4[C:23](=[O:35])[N:24]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[N:25]([CH3:28])[C:26]=4[CH3:27])=[O:21])=[CH:15][CH:14]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:36][CH3:37].[CH3:38][C@H:39]1[CH2:41][O:40]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[OH:40][C@@H:39]([CH3:41])[CH2:38][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]4[C:23](=[O:35])[N:24]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:25]([CH3:28])[C:26]=4[CH3:27])=[O:21])=[CH:17][CH:18]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:36][CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146262(2S)-2-MethyloxiraneHCID 136350301N-(4-((7-hydroxy-6-methoxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 60172850HCID 60172850, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

The title compound was prepared according to the procedure described in Example 15 by using N-(4-((7-hydroxy-6-methoxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (4.93 g, 9.93 mmol), (S)-2-methyloxirane (8.8 mL, 150 mmol) and K2CO3 (2.74 g, 19.8 mmol) in DMF/H2O (21 mL/4 mL). The title compound was purified by a silica gel column chromatography (DCM/MeOH=50/1 to 20/1) and was obtained as a pale solid (2.1 g, 38.3%).

Workup

  1. customThe title compound was purified by a silica gel column chromatography (DCM/MeOH=50/1 to 20/1)

Sources & evidence

ORD record
ord-ed19b2e4db324ad4aa23c539a544bfc6
Source dataset
uspto-grants-2015_09
Patent number
US09133162B2

Reaction notes

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