Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → tert-butyl 3-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate

Participants

Reaction Steps

3-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid was dissolved in DMF (5 mL). HATU (914 mg, 2.4 mmol) and DMAP (196 mg, 1.6 mmol) were added, and the reaction stirred at rt for 2 h. The solution was concentrated in vacuo and purified by preparative HPLC eluting with a gradient of 30% to 50% Solvent B in Solvent A to give 123 mg of the title compound as a light yellow solid. 1H NMR (400 MHz, CD3OD) δ 1.48 (s, 9 H) 1.59-1.70 (m, 1 H) 1.88 (d, J=13.39 Hz, 1 H) 1.95-2.02 (m, 1 H) 2.06 (dd, J=12.25, 3.92 Hz, 1 H) 2.75 (br. s., 1 H) 3.15 (t, J=11.62 Hz, 1 H) 4.04-4.20 (m, 2 H) 4.51 (br. s., 1 H) 4.93-5.14 (m, 2 H) 7.44 (s, 1 H) 7.58 (d, J=5.31 Hz, 1 H) 8.43 (d, J=5.56 Hz, 1 H). [M+H] found 357.

Provenance & Evidence