Ammonium formate → HCID 18327476, compound

Participants

Reaction Steps

A solution of 2-chloro-9-methoxybenzo[h]-5,6-dihydroquinazoline (50 mg, 0.20 mmol) and 1-[2-(4-amino-2,6-dimethylphenoxy)ethyl]pyrrolidine (47 mg, 0.20 mmol) in ethoxyethanol (2 ml) was treated with hydrogen chloride (0.2 ml of 1.0M HCl in diethyl ether, 0.20 mmol). The resulting mixture was heated at reflux for 6 h, then allowed to cool to room temperature. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic phase dried (MgSO4) and evaporated. The residue was subjected to column chromatography (3-6% methanol-dichloromethane) to afford the title compound as an off-white solid (37 mg) m.p. 123-126°. δH(d6DMSO) 9.28 (1H, s), 8.36 (1H, s), 7.76 (1H, d, J 2.8 Hz), 7.51 (2H, s), 7.26 (1H, d, J 8.3 Hz), 7.01 (1H, dd, J 8.3, 2.8 Hz), 3.85 (3H, s), 3.82 (2H, m), 3.31-2.60 (1H, m), 2.23 (6H, s) and 1.73 (4H, m). 1-[2-(4-amino-2,6-dimethylphenoxy)ethyl]pyrrolidine was prepared by treating a degassed stirring solution of 1-[2-(2,6-dimethyl-4-nitrophenoxy)ethyl]pyrrolidine (824 mg, 3.12 mmol) in ethanol (8 ml) with ammonium formate (590 mg, 9.36 mmol) and 10% palladium on charcoal (100 mg) for 8 h. The mixture was filtered through Celite® and evaporated. The residue was subjected to column chromatography (2-6% methanoldichloromethane) to afford the desired product (489 mg) as a pale yellow oil. 8H (CDCl3) 6.33 (2H, s), 3.84 (2H, t, J 6.3 Hz), 3.38 (2H, br s), 2.90 (2H, t, J 6.3 Hz), 2.65 (4H, m), 2.20 (6H, s) and 1.83 (4H, m). MS (ES+) 235 (MH+)

Provenance & Evidence