Dimethyl Sulfoxide → HCID 53237973, compound

HRID 1187311Notes

Reaction equation

Cl[C:2]1[C:3]2[C:10]([C:11]([C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=3[F:19])=[O:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.CS(C)=O.[C-:39]#[N:40].[K+]>O>[C:39]([C:2]1[C:3]2[C:10]([C:11]([C:13]3[C:14]([F:34])=[C:15]([NH:20][S:21]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:29]=4)(=[O:22])=[O:23])[CH:16]=[CH:17][C:18]=3[F:19])=[O:12])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)#[N:40]

Participants

Conditions

Temperature: 150 °C

Procedure

To N-[3-(4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-2,4-difluoro-phenyl]-4-trifluoromethyl-benzenesulfonamide (P-1016, 62 mg, 0.12 mmol), 1.00 mL of dimethyl sulfoxide is added, followed by potassium cyanide (39.0 mg, 0.60 mmol). The reaction is heated at 150° C. in an oil bath for 4 hours, then at 150° C. overnight. The reaction is poured into water and extracted with ethyl acetate. The organic layer is concentrated under vacuum and purified by silica gel column chromatography, eluting with a gradient of 10-60% ethyl acetate in hexanes. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (P-1023, 8 mg). MS (ESI) [M+H+]+=508.1.

Workup

customat 150° C.
customovernight
extractionextracted with ethyl acetate
concentrationThe organic layer is concentrated under vacuum
custompurified by silica gel column chromatography
washeluting with a gradient of 10-60% ethyl acetate in hexanes
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-fb849beff36c4122bd11d9587028bdff
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673928B2

Reaction notes

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