Hydrochloric Acid → HCID 131724554, compound

Participants

Reaction Steps

To a solution of (±)-cis 5,6,8a,9,10,11,12,12a-octahydro-4H,8H-quino[1,8-bc]-2,6-naphthyridine free base from EXAMPLE 123 (50 mg, 0.22 mmol) in 10 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.05 mL, 0.58 mmol) and sodium triacetoxyborohydride (0.19 g, 0.87 mmol) and a couple drops of acetic acid. The resulting mixture was stirred at ambient temperature for 1 h and then the reaction was quenched with water. The mixture was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. The residue (40 mg, 0.16 mmol) was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (0.25 mL, 0.5 mmol). A solid precipitated out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford the title compound of EXAMPLE 125 as an off white powder. 1H NMR (dmso-D6) δ: 10.65 (broad s, 1H), 6.77 (d, 1H, J=7.0 Hz), 6.73 (d, 1H, J=7.7 Hz), 6.47 (t, 1H, J=7.4 Hz), 3.45-3.35 (m, 1H), 3.30-2.85 (overlapping m, 8H), 2.80-2.58 (m, 8H), 2.35-2.25 (m, 1H), 2.22-2.15 (m, 1H), 1.90-1.75 (m, 3H). LRMS (ES)+: 243.4 (M+H)+.

Provenance & Evidence