Methanol → HCID 69521137, compound

Participants

Reaction Steps

The product of Example 29A (284 mg, 1.0 mmol) was treated with phenol (Aldrich, 188 mg, 2 mmol) according to the procedure of Example 14C. The free base of the title compound was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3H2O, 90:10:2, Rf. 0.15) as an oil (42 mg, yield, 14%). The free base of the title compound (42 mg, 0.14 mmol) in ethyl acetate:MeOH (3 mL, 10:1) was treated with fumaric acid (18 mg, 0.15 mmol) at room temperature for 10 hours. The title compound was obtained as a solid (22 mg, 36%). 1H NMR (MeOH-d4, 300 MHz) δ 1.84–2.18 (m, 3H), 2.25–2.38 (m, 1H), 2.50–2.58 (m, 1H), 3.23–3.44 (m, 5H), 3.80–3.88 (m, 1H), 5.32 (m, 1H), 6.69 (s, 2.5H), 7.00–7.06(m, 2H), 7.15–7.20 (m, 2H), 8.39 (s, 2H) ppm. MS (DCl/NH3) m/z 298 (M+H)+. Anal. Calculated for C17H19N3O2.1.26C4H4O4: C, 59.67; H 5.46; N, 9.47. Found: C, 59.43; N, 9.51.

Provenance & Evidence