1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 23511784, compound

Participants

Reaction Steps

To a stirred mixture of ethyl 5-[(2-pyrrolidinyl)methylamino]pyridine-2 carboxylate (230 mg, 0.923 mmol), 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (290 mg, 0.923 mmol), 4-DMAP (145 mg, 1.15 mmol) in DMF (7 ml) was added EDC.HCl (225 mg, 1.15 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 hr. The mixture was pored into ice-water. The solid was collected, washed with water and air-dried. The crude solid was purified by silica gel (30 ml) column chromatography with CHCl3-EtOH (98:2, v/v) as eluent to give ethyl 5-[[1-[3-methoxy4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]pyridine-2-carboxylate (400 mg, 80%) as fine needles. IR (KBr) n 3325, 1709, 1618, 1585, 1531 cm−; 1H-NMR (CDCl3) δ 1.39 (t, J=7 Hz, 3 H), 1.73–2.07 (series of m, 4 H), 2.28 (s, 3 H), 3.12 and 3.49 (each m, each 1 H), 3.60 (s, 2 H), 4.39 (br q, J=7 Hz, 2 H), 4.53 (m, 1 H), 6.07 (br s, 1 H), 6.23 (br s, 1 H), 6.75–6.77 (series of s and m, 2 H), 6.82 (dd, J=3.0 and 8.5 Hz, 1 H), 7.09–7.22 (series of m, 3 H), 7.49 (d, J=8.0 Hz, 1 H), 7.90 (d, J=8.5 Hz, 1H), 7.98 (d, J=2.6 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H); MS (FAB) m/z 546 (M++1); Anal. Calcd for C30H35N5O5.1.5×H2O: C, 52.92; H, 6.69; N, 12.23. Found: C, 63.11; H, 6.48; N, 11.96.

Provenance & Evidence