P-Toluenesulfonylhydrazide → HCID 68512118, compound

Participants

Reaction Conditions

Reaction Steps

A 100 mL round-bottomed flask was charged with tert-butyl 4-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.248 g, 0.455 mmol), 4-methylbenzenesulfonohydrazide (0.0846 g, 0.455 mmol) and toluene (10 mL). The reaction mixture was stirred at 100° C. for 4 days. The reaction was cooled to ambient temperature and partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated. The crude material was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford the product (84.3 mg, 33.9%). LRMS (APCI pos): >96% purity, 254 nm, m/e 548 (M+1).

Provenance & Evidence