Pyridine → HCID 131726133, compound

Participants

Reaction Steps

To a solution of 4-(5-methyl-2,5-diazabicyclo[2,2,1]hept-2-yl)-1-naphtylamine (0.210 g, 0.829 mmol) (prepared according to methods A and B), pyridine (468 μL, 5.80 mmol) in CH2Cl2 (3.0 mL) was added 4-methylbenzenesulfonyl chloride (0.158 g, 0.829 mmol) in CH2Cl2 (1.0 mL). The solution was stirred at room temperature for 16 hours and then concentrated. The crude product was purified via column chromatography (SiO2, CHCl3→CHCl3/MeOH/NH3 9:1:0.4%) to give the pure base which was converted to its HCl-salt: yield 160 mg (43%); 1H NMR (DMSO-d6) δ 10.78 (br s, 1H), 9.90–9.88 (m, 1H), 8.02–7.98 (m, 2H), 7.58–7.55 (m, 2H), 7.49–7.41 (m, 2H), 7.33–7.30 (m, 2H), 7.06–7.03 (m, 1H), 6.93–6.90 (m, 1H), 4.38–4.30 (m, 3H), 3.65–3.60 (m, 3H), 2.90–2.87 (m, 1H), 2.86–2.83 (m, 3H), 2.36 (br s, 2H), 2.35 (s, 3H); MS (posES-FIA) m/z=407.1655 (M+H)(calc 407.1667).

Provenance & Evidence