Cesium carbonate → HCID 57829251, compound

HRID 2356690Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:10]=2[CH2:11][N:12]2[C:16]([CH3:18])([CH3:17])[C:15](=[O:19])[N:14]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)[C:13]2=[O:31])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(#N)C>[F:36][C:34]1[CH:33]=[CH:32][C:10]([CH2:11][N:12]2[C:16]([CH3:18])([CH3:17])[C:15](=[O:19])[N:14]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:29])([F:30])[F:28])[CH:21]=3)[C:13]2=[O:31])=[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:7][CH:6]=2)[CH:35]=1

Participants

Conditions

Temperature: 60 °C

Procedure

150 mg of compound 240.1 were dissolved in 5 ml of acetonitrile and admixed with 145 mg of cesium carbonate and 41 mg of methanesulfonyl chloride. Subsequently, the mixture was stirred at 60° C. for 6 h; the next day, a further 1.2 equivalents of methanesulfonyl chloride were added and the mixture was stirred at 60° C. for a further 8 h. For workup, the reaction mixture was filtered, the filtrate was concentrated under reduced pressure and the residue was purified by chromatography (method [RP1]). N-(4-{5-Fluoro-2-[3-(4-fluoro-3-trifluoromethylphenyl)-5,5-dimethyl-2,4-dioxoimidazolidin-1-ylmethyl]phenylamino}phenyl)methanesulfonamide was obtained. Molecular weight 582.13 (C26H23F5N4O4S); retention time Rt=3.88 min.

Workup

stirringthe mixture was stirred at 60° C. for a further 8 h
filtrationFor workup, the reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure
customthe residue was purified by chromatography (method [RP1])

Sources & evidence

ORD record: ord-2fac34d0648c41b2b44a894b9ec8cd8e
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759366B2

Reaction notes

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