Cesium carbonate → HCID 60172481, compound

HRID 2277375Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[C:24](=[O:36])[N:25]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:26]([CH3:29])[C:27]=2[CH3:28])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:43][C@@H:44]1[CH2:46][O:45]1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:20][C:21]([C:23]2[C:24](=[O:36])[N:25]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:26]([CH3:29])[C:27]=2[CH3:28])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:43][C@H:44]([OH:45])[CH3:46])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of N-(3-fluoro-4-((7-hydroxyquinolin-4-yl)oxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (100 mg, 0.21 mmol) and Cs2CO3 (337 mg, 1.03 mmol) in 10 mL DMF was added (R)-2-methyloxirane (5 mL, 71.60 mmol). The reaction was warmed to 40° C. and stirred for two days. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (1:15 (v/v) MeOH/DCM) to give the title compound as a white solid (60 mg, 54%).

Workup

concentrationThe mixture was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (1:15 (v/v) MeOH/DCM)

Sources & evidence

ORD record: ord-03b82796400740588e426cd954fa7889
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133162B2

Reaction notes

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