Cesium carbonate → HCID 66684940, compound

HRID 1517875Notes

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][C:43]1([O:46][C:47](=[O:49])[CH3:48])[CH2:45][CH2:44]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O>[C:47]([O:46][C:43]1([CH2:42][O:19][C:15]2[CH:14]=[C:13]3[C:18]([C:9]([O:8][C:7]4[CH:6]=[CH:5][C:4]([NH:20][C:21]([C:23]5[C:24](=[O:36])[N:25]([C:30]6[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=6)[N:26]([CH3:29])[C:27]=5[CH3:28])=[O:22])=[CH:3][C:2]=4[F:1])=[CH:10][CH:11]=[N:12]3)=[CH:17][CH:16]=2)[CH2:45][CH2:44]1)(=[O:49])[CH3:48]

Participants

Conditions

Temperature: 40 °C

Procedure

To a mixture of compound N-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-1,5-di-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (342 mg, 0.708 mmol) and (1-acetoxycyclopropyl)methyl methanesulfonate (1.77 mmol) in 5 mL of DMA was added Cs2CO3 (2.8 g, 8.85 mmol). After stirring at 40° C. for 1 day, the reaction mixture was concentrated in vacuo and the residue was chromatographed on a silica gel column (50:1 (v/v) CH2Cl2/CH3OH) to give the title compound as a white solid (110 mg, 26%).

Workup

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

Sources & evidence

ORD record: ord-7fd07bf2522e4ce79ba155f87c2ef1b5
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232294B2

Reaction notes

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