Triethylamine → HCID 69591791, compound

Participants

Reaction Conditions

Reaction Steps

(3-Amino-propyl)-carbamic acid tert-butyl ester (Fluka, 0.054 ml, 0.31 mmol) was added to a solution of 3-benzyl-2-(1-methanesulfonyloxy-propyl)-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazine-5-carboxyic acid methyl ester (0.086 g, 0.21 mmol) and triethylamine (0.086 mL, 0.616 mmol) in DMF (1.0 mL) and the reaction mixture was heated to 75° C. for 4 h. The reaction mixture was quenched with saturated NaHCO3 (2 mL) and extracted with EtOAc (3×10 mL). The combined organic extracts were washed with 10% LiCl (4×10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 8/1 to 1/1 hexane/EtOAc to afford the title compound (0.013 g, 14%) as a solid: 1H NMR (CDCl3) δ 6.98–7.26 (m, 8H), 5.75 (m, 1H), 4.95 (m, 2H), 3.86 (s, 3H), 3.65 (m, 1H), 3.00 (m, 2H), 2.45 (m, 1H), 2.00 (m, 1H), 1.50–1.75 (m, 4H) 1.36 (s, 9H), 0.88 (m, 3H); MS (ESI+) 498 (M++H); HRMS (ESI+) calculated: 498.2716 (M++H), found: 498.2720 (M++H).

Provenance & Evidence