1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274411, compound

Participants

Reaction Conditions

Reaction Steps

(Z)—N-Hydroxy-6-(trifluoromethyl)nicotinimidamide (0.082 g, 0.399 mmol), 2-(3-(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.086 g, 0.363 mmol; Example 216A) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.104 g, 0.544 mmol) were stirred together in dichloroethane (1 mL) at room temperature for 4 hours. The reaction was heated to 85° C. and heated overnight. The reaction was cooled, loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=36 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 9.41 (d, J=1.7, 1H), 8.58-8.50 (m, 1H), 7.84 (dd, J=0.5, 8.1, 1H), 7.33-7.26 (m, 2H), 7.11-7.01 (m, 2H), 4.98 (d, J=17.0, 1H), 4.87 (d, J=17.0, 1H), 3.78 (t, J=9.0, 1H), 3.74-3.61 (m, 2H), 2.67 (dddd, J=4.3, 7.0, 9.1, 13.2, 1H), 2.26 (ddd, J=8.5, 13.0, 16.5, 1H); MS (ESI+) m/z 407.0 (M+H)+.

Provenance & Evidence