Methyl vinyl sulfone → HCID 54762051, compound

HRID 929980Notes

Reaction equation

Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:35])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]4[CH2:33][CH2:32][NH:31][CH2:30]4)=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:36][S:37]([CH:40]=[CH2:41])(=[O:39])=[O:38]>C1COCC1>[C:2]([C:6]1[O:10][N:9]=[C:8]([NH:11][C:12](=[O:35])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:34])[C:22]3[CH:27]=[CH:26][C:25]([O:28][CH:29]4[CH2:33][CH2:32][N:31]([CH2:41][CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:30]4)=[CH:24][N:23]=3)=[CH:16][CH:15]=2)[CH:7]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(4-(3-(5-tert-Butylisoxazol-3-yl)ureido)phenyl)-5-(pyrrolidin-3-yloxy)picolinamide hydrochloride (150 mg, 0.30 mmol) was suspended in 3 mL of THF at rt. Methylsulfonylethene (29 μL, 0.33 mmol) and TEA (126 μL, 0.90 mmol) were added sequentially. The resulting mixture was heated at 60° C. for 1 h, then heated at 52° C. for 60 h. LC-MS indicated the reaction was complete. The organic solvent was evaporated under reduced pressure and the residue was purified by reverse phase HPLC to give N-(4-(3-(5-tert-butylisoxazol-3-yl)ureido)phenyl)-5-(1-(2-(methylsulfonyl)ethyl)pyrrolidin-3-yloxy)picolinamide (136 mg, 79%). LC-MS (ESI) m/z 571 (M+H)+.

Workup

temperatureheated at 52° C. for 60 h
customThe organic solvent was evaporated under reduced pressure
customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-24c33d18200344c9b6122cda5ba63566
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296722B2

Reaction notes

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