5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide → 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylbenzenesulfonamide

Participants

Reaction Steps

5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methyl-2-nitrobenzenesulfonamide (Intermediate 17A) (1.0 g, 2.94 mmol) was dissolved in 2M ammonia in methanol (110 mL). The resulting solution was hydrogenated using the H-cube at 40° C. under 30 bar pressure of hydrogen, with a flow rate of 1 mL per minute through a 10% palladium on charcoal cartridge. The reaction mixture was purified by SCX and evaporated to afford 2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-N-methylbenzenesulfonamide, (868 mg, 2.8 mmol). 1H NMR; δ (ppm)(CHCl3-d): 7.17 (1H, d, J=3.01 Hz), 6.88 (1H, dd, J=9.04, 3.01 Hz), 6.72 (1H, d, J=9.04 Hz), 4.82 (1H, bs), 4.31 (2H, bs), 3.88-3.87 (1H, m), 3.42-3.39 (2H, m), 3.13-2.97 (6H, m), 2.57 (3H, d, J=3.51 Hz), 2.11-2.04 (2H, m), 1.76-1.68 (2H, m).

Provenance & Evidence