4-Aminobenzonitrile → (R)-2-(6-chloro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-N-(4-cyanophenyl)-3-methylbutanamide

Participants

Reaction Steps

To an 8 mL scintillation vial equipped for stirring was added (R)-2-(6-chloro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-3-methylbutanoic acid (10 mg, 0.032 mmol). THF (0.5 mL), 4-aminobenzonitrile (7.68 mg, 0.065 mmol) and HATU (14.83 mg, 0.039 mmol) were added and the solution was stirred at 25° C. for 1 h. The reaction mixture was purified via preparative mass trigger LC-MS (AcCN/H2O, 5-50%). The fractions were collected, concentrated, and dried in vacuo to afford the title compound as a yellow oil (2 mg, 15.1%). 1H NMR (400 MHz, CD3OD) δ 0.90-1.03 (m, 3 H) 1.07-1.15 (m, 3 H) 2.59 (dt, J=11.24, 6.63 Hz, 1 H) 5.01 (d, J=19.45 Hz, 1 H) 5.21 (d, J=11.12 Hz, 1 H) 5.42 (d, J=19.45 Hz, 1 H) 7.64-7.66 (m, 1 H) 7.66-7.68 (m, 1 H) 7.80-7.82 (m, 1 H) 7.82-7.84 (m, 1 H) 7.86 (s, 1 H) 8.25 (s, 1 H). [M+H] calc'd for C21H18ClN5O2, 408; found, 408.4.

Provenance & Evidence