1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274210, compound

Participants

Reaction Steps

To a solution of bis(4-fluorophenyl)(piperidin-4-yl)methanol (0.30 g, 1.00 mmol, Example 32A) in dichloromethane (20 mL) was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) under nitrogen. To the mixture was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (6.1 mg, 0.005 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated, and the residue was partitioned in ethyl acetate:water (8:2). The organic layer was separated, washed with water and then brine, dried over MgSO4, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexanes (1:1) gave the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.49-7.57 (m, 4H), 7.17-7.35 (m, 10H), 7.06-7.13 (m, 4H), 5.49 (s, 1H), 4.36 (d, J=14.0 Hz, 1H), 4.17 (d, J=16.6 Hz, 1H), 4.10 (d, J=15.7 Hz, 1H), 3.81 (d, J=14.3 Hz, 1H), 3.34 (t, J=6.7 Hz, 2H), 2.95-2.98 (m, 1H), 2.73-2.85 (m, 1H), 2.72 (t, J=6.6 Hz, 2H), 2.50-2.62 (m, 1H), 1.20-1.39 (m, 4H).

Provenance & Evidence