Cesium carbonate → HCID 46201940, compound

HRID 1969397Notes

Reaction equation

HRID 1969397 reaction equation
[CH2:1]1[C:3]2([CH2:7][CH:6](CS([O-])(=O)=O)[CH2:5][O:4]2)[CH2:2]1.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([O:24][C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]4[C:35](=[O:47])[N:36]([C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[N:37]([CH3:40])[C:38]=4[CH3:39])=[O:33])=[CH:27][C:26]=3[F:48])=[CH:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:49][CH3:50].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C>[CH2:2]1[C:3]2([CH2:7][CH:6]([O:13][C:14]3[CH:23]=[C:22]4[C:17]([C:18]([O:24][C:25]5[CH:30]=[CH:29][C:28]([NH:31][C:32]([C:34]6[C:35](=[O:47])[N:36]([C:41]7[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=7)[N:37]([CH3:40])[C:38]=6[CH3:39])=[O:33])=[CH:27][C:26]=5[F:48])=[CH:19][CH:20]=[N:21]4)=[CH:16][C:15]=3[O:49][CH3:50])[CH2:5][O:4]2)[CH2:1]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86640794HCID 86640794, compoundHCID 136341072N-(3-fluoro-4-(7-hydroxy-6-methoxyquinolin-4-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 46201940HCID 46201940, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a mixture of (4-oxaspiro[2.4]heptane-6-yl)methanesulfonate (168 mg, 0.877 mmol) and N-(4-(7-hydroxy-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)-2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazole-4-carboxamide (300 mg, 0.584 mmol) in 5 mL of N,N-dimethylacetamide was added cesium carbonate (893 mg, 2.74 mmol, Aladdin). After stirring at rt for 4 hrs, the reaction was warmed to 40° C. and stirred for 16 hrs. The reaction mixture was concentrated in vacuo and chromatographed with a silica gel column (5:1 (v/v) EtOAc/n-hexane) to afford the title compound as a white solid (65 mg, 18%).

Workup

  1. temperaturethe reaction was warmed to 40° C.
  2. stirringstirred for 16 hrs
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customchromatographed with a silica gel column (5:1 (v/v) EtOAc/n-hexane)

Sources & evidence

ORD record
ord-0d830283f4684e4e97a2406b23edae6e
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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