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)methyl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

3-(((1-(tert-Butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid was dissolved in DMF (3 mL). HATU (158 mg, 0.417 mmol) and DMAP (40 mg, 0.278 mmol) were added, and the reaction was stirred at rt for 2 h, concentrated in vacuo, and purified by preparative HPLC eluting with a gradient of 30% to 50% Solvent B in Solvent A to give 14.5 mg of the title compound as a light brown oil. 1H NMR (400 MHz, CD3OD) δ 1.46 (br. s., 9 H) 1.70-1.81 (m, 1 H) 1.99-2.11 (m, 1 H) 2.78 (dt, J=14.34, 7.11 Hz, 1 H) 3.11-3.22 (m, 1 H) 3.32-3.36 (m, 1 H) 3.47-3.57 (m, 2 H) 3.72 (d, J=7.33 Hz, 1 H) 3.76-3.89 (m, 1 H) 5.09 (s, 2 H) 7.38 (s, 1 H) 7.51 (d, J=5.31 Hz, 1H) 8.42 (d, J=5.56 Hz, 1 H). [M+H] found 357.

Provenance & Evidence