Hydrochloric Acid → HCID 18470790, compound

Participants

Reaction Steps

Benzyl-2-[3-chloro-2-methyl-5-[(3{[methyl(2,2,2-trifluoroacetyl)amino]methyl}phenethyl)amino]-6-oxo-1(6H) pyrazinyl]acetate (preparation 37) (200 mg, 0.36 mmol) was dissolved in methanol (80 ml), treated with Pearlman's catalyst (80 mg) and stirred under a hydrogen atmosphere (60 psi, room temperature, 2.5 hr). The catalyst was removed by filtration, followed by evaporation of the solvent and azeotroping with CH2Cl2 to yield a crude solid. To the crude mixture, (3-methyl-1H-indol-5-yl)methylamine (preparation 36) (60 mg, 0.37 mmol), HOBT (56 mg, 0.41 mmol), WSCDI.HCl (91 mg, 0.47 mmol), N-methylmorpholine (0.073 ml, 0.66 mmol) and DMF (10 ml) were added and stirred at room temperature for 18 hr. The resultant mixture was evaporated to dryness and triturated with water. The brown solid was filtered, dried, then purified by chromatography (SiO2, gradient elution with 1:2 ethyl acetate:hexane; 2:1 ethyl acetate:hexane) to give the desired product (42 mg, 20%). 1H NMR (CD3OD) δ 2.15 (s, 3H), 2.30 (s, 3H), 2.85-3.20 (m, 3H), 3.35 (s, 2H), 3.60 (m, 2H), 4.50 (s, 2H), 4.604.65 (m, 2H), 4.75 (s, 2H), 6.65 (s, 1H), 6.95-7.50 (m, 8H). LRMS m/z=596.5 (M+1)+.

Provenance & Evidence