Methylamine → HCID 67052519, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (1E,4E)-1,5-di(pyridin-3-yl)penta-1,4-dien-3-one (1 g, 3.2 mmol) in DMF (10 mL) was treated with N-methylamine (40% in H2O, 2.8 mL, 32 mmol) at 0° C. The solution was stirred for 6 h at 0° C. The reaction mixture was poured into ice-water (150 mL) and was extracted with DCM. The combined organic layers were dried with MgSO4, filtered and evaporated in vacuo. The crude product was purified by flash-chromatography (CH2Cl2/MeOH 9:1) to obtain NW-B593 as a bright yellow solid (814 mg, 94%). mp: 103-106° C. 1H NMR (300 MHz, CDCl3) δ (ppm): 8.67 (d, 4J=1.8 Hz, 2H, HAr), 8.59 (dd, 3J=4.8 Hz, 4J=1.6 Hz, 2H, HAr), 7.85 (d, 3J=7.9 Hz, 2H, HAr), 7.37 (dd, 3J=7.9 Hz, 3J=4.8 Hz, 2H, HAr), 3.58 (dd, 3J=12.0 Hz, J=2.8 Hz, 2H, CH2), 2.84 (t, 3J=13.0 Hz, 2H, CH), 2.55 (dd, 3, J=13.9 Hz, J=1.8 Hz, 2H, CH2), 1.64 (s, 3H, CH3). 13C NMR (75 MHz, CDCl3) δ (ppm): 204.9 (C), 149.4 (CH), 148.8 (CH), 138.1 (C), 134.8 (CH), 124.1 (CH), 67.5 (CH), 50.2 (CH2), 41.0 (CH3). MS (FAB) m/z: 268.2 (M+). Anal. calcd for C16H17N3O.0.3H2O: C, 70.46; H, 6.50; N, 15.41. Found: C, 70.45; H, 6.38; N, 15.32%.

Provenance & Evidence