Cesium carbonate → HCID 46203252, compound

HRID 1969377Notes

Reaction equation

CS([O:5][CH2:6][C@@H:7]1[CH2:13][CH2:12][C:9]2([CH2:11][CH2:10]2)[N:8]1[CH3:14])(=O)=O.O[C:16]1[CH:25]=[C:24]2[C:19]([C:20]([O:26][C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]4[C:37](=[O:49])[N:38]([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[N:39]([CH3:42])[C:40]=4[CH3:41])=[O:35])=[CH:29][C:28]=3[F:50])=[CH:21][CH:22]=[N:23]2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH3:14][N:8]1[C@H:7]([CH2:6][O:5][C:16]2[CH:25]=[C:24]3[C:19]([C:20]([O:26][C:27]4[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]5[C:37](=[O:49])[N:38]([C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)[N:39]([CH3:42])[C:40]=5[CH3:41])=[O:35])=[CH:29][C:28]=4[F:50])=[CH:21][CH:22]=[N:23]3)=[CH:18][CH:17]=2)[CH2:13][CH2:12][C:9]21[CH2:11][CH2:10]2

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of ((5S)-4-methyl-4-azaspiro[2.4]heptane-5-yl)methyl methanesulfonate (150 mg, 0.685 mmol) and N-(4-(7-hydroxyquinolin-4-yloxy)-3-fluorophenyl)-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxamide (331.5 mg, 0.685 mmol) in 8 mL of N,N-dimethylacetamide was added cesium carbonate (893 mg, 2.74 mmol, Aladdin). After stirring at 40° C. for 3 days, the reaction mixture was concentrated in vacuo and the residue was chromatographed with a silica gel column (50:1 (v/v) CH2Cl2/CH3OH) to give the desired product as a pale yellow solid (25 mg, 6%).

Workup

concentrationthe reaction mixture was concentrated in vacuo
customthe residue was chromatographed with a silica gel column (50:1 (v/v) CH2Cl2/CH3OH)

Sources & evidence

ORD record: ord-ff5dfd6c511e4315a17eccaf2d160b9e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426585B2

Reaction notes

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