Methanol → HCID 131728506, compound

Participants

Reaction Conditions

Reaction Steps

Tetrahydrofurfurylamine (0.776 mL, 7.5 mmol) was added to a mixture of Example 102j (0.6 g, 1.25 mmol) and tetrabutylammonium iodide (0.004 g) in methanol (5 mL), under argon, in a pressure reactor vessel heated at 110° C. for 5 h. The reaction mixture was cooled, concentrated, treated with methanolic HCl (15 mL) and refluxed for 4 h. The reaction mixture was cooled, concentrated and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as an off-white solid. Yield: 0.332 g, (51%); 1H NMR (DMSO-d6): δ 1.5 (m, 2H, CH2), 1.78 (m, 2H, CH2), 1.92 (m, 2H, CH2), 2.67 (s, 3H, CH3), 3.19 (t, 4H, 2CH2), 3.63 (q, 1H, CH2), 3.78 (q, 1H, CH2), 3.9 (s, 3H, OCH3), 3.99 (m, 2H, CH2), 5.17 (s, 2H, CH2), 7.6 (d, 1H, Ar), 7.15 (d, 1H, Ar), 8.11 (s, 1H, Ar), 8.16 (s, 1H, Ar); MS: m/e (ES+) 522 (M+1).

Provenance & Evidence