Cesium carbonate → HCID 59278563, compound

HRID 1517864Notes

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.CS(O[CH2:42][CH2:43][C:44]1([OH:47])[CH2:46][CH2:45]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)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][CH2:42][CH2:43][C:44]3([OH:47])[CH2:46][CH2:45]3)=[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-yloxy)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (735.7 mg, 1.52 mmol) and 2-(1-hydroxycyclopropyl)ethyl methanesulfonate (3.04 mmol) in 8 mL of N,N-dimethylacetamide was added cesium carbonate (4.955 g, 15.2 mmol). After stirring at 40° C. for 1 day, the reaction was quenched with water (5 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was chromatographed on a silica gel column (CH2Cl2/CH3OH (v/v)=45:1) to afford the title compound as a white solid (270 mg, 15.6%).

Workup

customthe reaction was quenched with water (5 mL)
extractionextracted with CH2Cl2 (20 mL×3)
dry with materialThe combined organic phases were dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on a silica gel column (CH2Cl2/CH3OH (v/v)=45:1)

Sources & evidence

ORD record: ord-f6971b03c2bc4b5d880a9c36f154ccba
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232294B2

Reaction notes

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