Sulfanilamide → 4-(4-(4-(Aminomethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)benzenesulfonamide

Participants

Reaction Steps

To a flask containing tert-butyl(1-(2-(4-sulfamoylphenylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (0.215 g, 0.428 mmol, prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with 4-(tert-butoxycarbonylaminomethyl)piperidine [Tyger] and B with 4-aminobenzenesulfonamide) was slowly added a 20% TFA/DCM (3 mL) solution. The mixture was stirred at rt for about 4 h. The solvent was removed in vacuo and the residue purified by reverse phase preparatory HPLC (Table 2, method b) to provide 4-(4-(4-(aminomethyl)piperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)benzenesulfonamide (0.142 g, 63%): LC/MS (Table 2, Method a) Rt=0.20 min; MS m/z 403.2 (M+H)+. Syk IC50=A

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