Tert-Butyl nitrite → 1-Methoxy-9-trifluoromethyl-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-N-(4-methoxy-quinolin-8-yl)-4-trifluoromethyl-benzenesulfonamide (Intermediate 196) (454 mg, 1.1 mmol) in AcOH/THF (1:1, 10 ml) was cooled to 0° C. and tert-butylnitrite (235 mg, 2.2 mmol) was added. The reaction was stirred at 0-5° C. for 2 h. The reaction was quenched water (5 ml) and the solvent partially evaporated. The residue was dissolved in EtOAc (150 ml), washed with sat. sodium bicarbonate solution, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM/MeOH (1:0-99:1) gradient elution followed by recrystallisation from iPA/MeCN to give the title compound (45 mg, 11%).

Provenance & Evidence