Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → (R)-2-(6-chloro-3-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)-N-((S)-1-cyanobutan-2-yl)-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), (S)-3-aminopentanenitrile (3.19 mg, 0.032 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 (3.1 mg, 24.6%). 1H NMR (400 MHz, CD3OD) δ 0.93 (d, J=6.57 Hz, 3 H) 0.97 (t, J=7.33 Hz, 3 H) 1.07 (d, J=6.57 Hz, 3 H) 1.51-1.69 (m, 2 H) 2.44-2.58 (m, 2 H) 2.58-2.72 (m, 1 H) 4.07 (br. s., 1 H) 4.86-4.97 (m, 1 H) 5.08 (d, J=11.12 Hz, 1 H) 5.31 (d, J=19.71 Hz, 1 H) 7.84 (s, 1 H) 8.23 (s, 1 H). [M+H] calc'd for C19H22ClN5O2, 388; found, 388.4.

Provenance & Evidence