Cesium carbonate → N-(5-(7-(3-(1-hydroxycyclopropyl)propoxy)quinolin-4-yloxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 1969401Notes

Reaction equation

HRID 1969401 reaction equation
[OH: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:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)[N:25]([CH3:28])[C:26]=4[CH3:27])=[O:21])=[N:17][CH:18]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].CS(O[CH2:47][CH2:48][CH2:49][C:50]1([OH:53])[CH2:52][CH2:51]1)(=O)=O>CC(N(C)C)=O>[OH:53][C:50]1([CH2:49][CH2:48][CH2:47][O:1][C:2]2[CH:11]=[C:10]3[C:5]([C:6]([O:12][C:13]4[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]5[C:23](=[O:35])[N:24]([C:29]6[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=6)[N:25]([CH3:28])[C:26]=5[CH3:27])=[O:21])=[N:17][CH:18]=4)=[CH:7][CH:8]=[N:9]3)=[CH:4][CH:3]=2)[CH2:52][CH2:51]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86640796HCID 86640796, compoundHCID 136341064N-(5-(7-hydroxyquinolin-4-yloxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 59278542N-(5-(7-(3-(1-hydroxycyclopropyl)propoxy)quinolin-4-yloxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 62.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 9 by using N-(5-(7-hydroxyquinolin-4-yloxy)pyridin-2-yl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (277 mg, 0.593 mmol), Cs2CO3 (560 mg, 1.724 mmol, Aladdin), and 3-(1-hydroxycyclopropyl)propyl methanesulfonate (334 mg, 1.724 mmol) in DMA (10 mL). The title compound was purified by a silica gel column chromatography (67:30:1:2 (v/v/v/v) EtOAc/CH2Cl2/CH3OH/Et3N) to afford the title compound as a white solid (210 mg, 62.6%).

Workup

  1. customThe title compound was prepared
  2. customThe title compound was purified by a silica gel column chromatography (67:30:1:2 (v/v/v/v) EtOAc/CH2Cl2/CH3OH/Et3N)

Sources & evidence

ORD record
ord-426982ffa7384414b4f695077cc17ba9
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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