Formaldehyde → HCID 11212985, 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; 30 mg, 0.072 mmol) in 2:1 acetonitrile/DCM (6 mL), was added formaldehyde (0.1 mL, 3.6 mmol), sodium cyanoborohydride (68 mg, 1.08 mmol) and acetic acid (12 μL). The reaction mixture was stirred for 3 h at room temperature. 1 M NaOH was added until the solution became basic. The mixture was taken up in DCM (5 mL), and washed with water and brine. The organic layer was removed, dried, and purified by preparative reversed-phase HPLC (acetonitrile/water, 0.05% TFA) to afford the title compound (8 mg, 0.02 mmol, 25%). MS (ESI): m/z 446 [M+H]+, 468 [M+Na]+. HPLC (reversed-phase): RT=9.14 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.61 (s, 1H), 8.22 (dd, J=7.0 Hz, 1.0 Hz, 1H), 8.18 (dd, J=8.8 Hz, 1.0 Hz, 1H), 7.63 (dd, J=8.8 Hz, 7.0 Hz, 1H), 6.95 (d, J=2.5 Hz, 7 Hz, 1H), 6.90 (d, J=8.7 Hz, 1H), 6.26 (dd, 8.7 Hz, 2.5 Hz, 1H), 3.16 (s, 4H), 2.95 (s, 6H), 1.56 (m, 2H), 1.42 (m, 4H).

Provenance & Evidence