Trifluoroacetic acid → HCID 89784123, compound

Participants

Reaction Conditions

Reaction Steps

To NaH (60 wt % in mineral oil; 0.071 g, 1.763 mmol) in 1 mL DMF was added 5-aminopyrimidine (AK Scientific, Union City, Calif.; 0.168 g, 1.76 mmol). After 10 min, 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.075 g, 0.252 mmol) was added and the reaction became dark red. After 2 h, the reaction was cooled to 0° C. and TFA (0.136 ml, 1.763 mmol) was added along with 1 mL DMSO. The reaction was filtered, and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 10-60% ACN/H2O with 0.1% TFA); the product-containing fractions were concentrated in vacuo then treated with saturated aq. NaHCO3 and DCM. The organic layer was separated, and the aq. layer was extracted 3×DCM and 1× EtOAc. The combined organic layers were then treated with MeOH until the solid dissolved, dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give 2-(2-(pyrimidin-5-ylamino)quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.039 g, 0.109 mmol, 43% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 11.66 (1H, br. s), 9.84 (1H, s), 9.21 (2H, s), 8.82 (1H, s), 8.21 (1H, d, J=8.8 Hz), 7.83 (1H, dd, J=7.2, 1.6 Hz), 7.70 (1H, dd, J=8.0, 1.6 Hz), 7.37 (1H, t, J=7.6 Hz), 7.15 (1H, d, J=8.8 Hz), 6.82-6.95 (1H, m), 6.66 (1H, d, J=2.2 Hz), 3.37-3.54 (2H, m), 2.83 (2H, t, J=6.9 Hz). m/z (ESI, +ve) 357.0 (M+H)+.

Provenance & Evidence