Sodium Hydroxide → HCID 11295248, compound

Participants

Reaction Steps

To a stirred solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-amino-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 24; 50 mg, 0.12 mmol) in dichloroethane (4 mL) was added cyclohexanecarboxaldehyde (43 μL, 0.36 mmol), followed by sodium triacetoxyborohydride (50 mg, 0.24 mmol). The reaction mixture was stirred for 12 h at room temperature. 1 M NaOH was added until the solution became basic. The mixture was taken up in 5 mL of DCM and washed with water and aqueous NaHCO3. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC to afford the title compound (20 mg, 0.04 mmol, 33%). MS (ESI): m/z 514 [M+H]+, 536 [M+Na]+. HPLC (reversed-phase): RT=10.93 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.36 (s, 1H), 8.20 (dd, J=8.8, 7.0 Hz, 2H), 7.63 (dd, J=8.8, 7.0 Hz, 1H), 6.85 (d, J=3.8 Hz, 1H), 6.81 (d, J=2.3 Hz, 1H), 6.15 (dd, J=8.5, 2.3 Hz, 1H), 3.21 (m, 4H), 2.90 (d, J=6.7 Hz, 2H), 1.74 (m, 6H), 1.57 (m, 2H), 1.46 (m, 4H), 1.22 (m, 3H), 0.96 (m, 2H).

Provenance & Evidence