HCID 89783988, compound → HCID 89782250, compound

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Reaction Steps

The above-obtained brown solid 2-(2,4-dimethoxybenzyl)-7-(2-(morpholine-4-carbonyl)quinolin-8-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one (Example 167c) in 1 mL of TFA and 1 mL of DCM was heated in an oil bath at 50° C. for 1 h. The mixture was concentrated under reduced pressure. The orange residue was partitioned between 50 mL of EtOAc and 5 mL of 2 N NaOH. The EtOAc layer was washed with 10 mL of brine and concentrated. Purification of the brown residue on a silica gel column (1-10% MeOH in EtOAc) gave 7-(2-(morpholine-4-carbonyl)quinolin-8-yl)-3,4-dihydropyrrolo[1,2-a]pyrazin-1(2H)-one (80 mg, 0.213 mmol, 31% yield for 3 steps) as a tan crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.51 (1H, d, J=8.6 Hz), 8.07 (1H, dd, J=7.3, 1.3 Hz), 7.94 (1H, d, J=1.6 Hz), 7.86 (1H, m), 7.75 (2H, d, J=8.4 Hz), 7.67 (1H, t, J=7.7 Hz), 7.36 (1H, d, J=1.8 Hz), 4.23 (2H, m), 3.75 (4H, m), 3.64 (4H, m), 3.57 (2H, m). m/z (ESI, +ve) 377.0 (M+H)+.

Provenance & Evidence