4-Toluenesulfonyl chloride → N-(3-amino-propyl)-N-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynyl]-4-methyl-benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-{3-[(R)-1-(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3-ynylamino]-propyl}-isoindole-1,3-dione (52.6 mg, 0.10 μmol) in pyridine (0.5 mL) was treated with respective sulfonyl chloride (in this case 4-methyl benzenesulfonyl chloride, 0.25M solution in DMA/AcCN (1:1), 0.5 mL, 0.125 μmol). The mixture was stirred at 45° C. for 24 h. Solvent was removed under reduced pressure. Residue was taken in MeOH (1.0 mL) and treated with hydrazine (0.25 mL). Reaction mixture was stirred at room temperature for 16 h and solvent removed under reduced pressure. The product was purified with reverse phase chromatography to give final product. Yield (10.4 mg, 20%). LCMS: m/e 551 [M+H].

Provenance & Evidence