Triethylamine → HCID 69591863, compound

Participants

Reaction Steps

To a solution of (±)-N-{3-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-propylamino]-propyl}-carbamic acid tert-butyl ester (0.51 g, 1.08 mmol) and Et3N (0.25 mL, 1.79 mmol) in CH2Cl2 (10 mL) at rt was added p-toluoyl chloride (0.21 mL, 1.58 mmol) under N2 and stirred at rt for 3 hr. The reaction mixture was diluted with CH2Cl2 to 100 mL, washed with aq. NaHCO3 solution (30 mL), dried over MgSO4. Concentration and purification of the crude product by flash column chromatography (SiO2, EtOAc/hexane 1.5:8.5 to 1:3) gave the title compound as pale oil (0.43 g, 67%): 1H NMR (CDCl3) δ 7.30 (m, 2H), 7.24 (m, 1H), 7.15 (m, 2H), 7.10 (d, 1H, J=4.4 Hz), 6.53 (d, 1H, J=4.4 Hz), 5.91 (m, 1H), 4.95 (m, 1H), 3.35 (m, 2H), 2.70 (m, 1H), 2.36 (s, 3H), 2.05 (m, 1H), 1.95 (m, 1H), 1.43 (m, 3H), 1.35 (s, 9H), 0.67 (m, 3H); MS (ESI+) 592.15 (M++H).

Provenance & Evidence