1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274307, compound

Participants

Reaction Steps

To a solution of piperidin-4-ylbis(3-(trifluoromethyl)phenyl)methanol (0.40 mg, 1.00 mmol, Example 33A) 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 reaction 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 7.85-7.93 (m, 4H), 7.55-7.57 (m, 4H), 7.18-7.36 (m, 10H), 5.93 (s, 1H), 4.34-4.41 (m, 1H), 4.06-4.23 (m, 2H), 3.82 (d, J=13.5 Hz, 1H), 3.35 (t, J=6.9 Hz, 2H), 2.94-3.11 (m, 2H), 2.72 (t, J=6.4 Hz, 2H), 2.59-2.67 (m, 1H), 1.17-1.50 (m, 4H).

Provenance & Evidence