Water → HCID 67108746, compound

Participants

Reaction Conditions

Reaction Steps

Nitrogen (g) is bubbled through a solution of 1-(4-amino-quinazolin-7-ylmethyl)-piperazin-2-one (100 mg, 0.39 mmol), EXAMPLE 72, in 2 mL of CH3CN. After 5 min, acetic acid 3-(6-methoxy-pyridin-3-yl)-(E)-allyl ester (75 mg, 0.36 mmol, prepared as described in EXAMPLE 19 in 2 mL of CH3CN, palladium(II) acetate (catalytic amount), triphenylphosphine (catalytic amount), 2 mL of H2O and 0.5 mL of triethylamine are added to the solution. The mixture is heated at 80° C. for 1 hours. At this time, the mixture is cooled, filtered and concentrated in vacuo. The crude material is purified by RP-HPLC eluting in a gradient of 10% CH3CN/H2O (0.1% TFA) to 60% CH3CN/H2O (0.1% TFA) and the appropriate product fractions are combined and lyopholized to give the title compound (44 mg, 0.07 mmol) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ9.86 (s, 1H), 9.79 (s, 1H), 8.83 (s, 1H), 8.40 (d, 1H), 8.25 (s, 1H), 7.95 (d, 1H), 7.75 (s, 1H), 7.63 (d, 1H), 6.86 (d, 1H), 6.82 (d, 1H), 6.32 (dt, 1H), 4.78 (s, 2H), 3.98 (s, 2H), 3.93 (m, 2H), 3.85 (s, 3H), 3.53 (m, 4H). ESI MS, [M+H]+=405.

Provenance & Evidence