Dimethylamine → HCID 25254371, compound

Participants

Reaction Steps

Example 8a (50 mg, 0.10 mmol) was reacted with 1.0 M solution of dimethylamine in THF (1 mL, 1 mmol) at 55° C. at for 24 h. The solvent was removed under vacuum and the crude mixture was suspended in Et2O (910 mL) and 2N HCl (10 mL). The ethereal layer was separated, dried over MgSO4 and evaporated to dryness. The isolated white solid was again suspended in mixture of Et2O and hexane (1/9) sonicated for 1 minute and solid was filtered and dried. The isolated solid was suspended in DCM and washed with NaHCO3 (aq) solution. The organic layer was dried over MgSO4 and evaporated to dryness to afford the title compound as a pale yellow oil (26 mg, 56%). 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 7.00-6.95 (m, 2H), 4.05 (t, J=6.0 Hz, 2H), 3.96 (t, J=6.6 Hz, 2H), 3.82 (s, 3H), 3.03-2.96 (m, 1H), 2.57 (t, J=6.0 Hz, 2H), 2.49 (s, 3H), 2.27 (s, 6H), 2.18 (s, 3H), 2.03-1.98 (m, 2H), 1.29 (d, J=6.9 Hz, 3H). MS (ES+) m/z 452.2.2 (M+H+).

Provenance & Evidence