Trifluoroacetic acid → HCID 89783521, compound

Participants

Reaction Conditions

Reaction Steps

Phenylmethanamine (0.144 g, 1.343 mmol) and 2-(2-chloroquinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1; 0.100 g, 0.336 mmol) were combined in 1 mL DMF, sealed, and heated to 100° C. overnight. The mixture was treated with TFA (0.104 ml, 1.343 mmol) and was diluted with 1 mL DMSO, filtered and purified by rpHPLC (Phenomenex Gemini 150×30 mm C18 column, 5-60% ACN/H2O with 0.1% TFA); product-containing fractions were treated with saturated aq. NaHCO3 and DCM. The organic layer was separated and the aq. layer was extracted 3×DCM. The combined organic layers were then dried over Na2SO4, filtered, and concentrated in vacuo to give 2-(2-(benzylamino)-quinolin-8-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (0.011 g, 0.030 mmol, 9% yield) as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.45 (1H, br. s), 7.88-8.01 (3H, m), 7.50 (1H, dt, J=7.7, 0.7 Hz), 7.39-7.45 (2H, m), 7.34 (2H, t, J=7.5 Hz), 7.21-7.28 (1H, m), 7.18 (1H, t, J=7.6 Hz), 6.88-7.00 (3H, m), 4.71 (2H, d, J=5.9 Hz), 3.34-3.38 (2H, m), 2.56-2.65 (2H, m). m/z (ESI, +ve) 369.0 (M+H)+.

Provenance & Evidence