N,N,N',N'-Tetramethylmethanediamine → HCID 66599777, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3H-imidazo[4,5-b]pyridine (4.65 g, 10.2 mmol) in CH2Cl2 (50 mL) was added potassium carbonate (1.60 g, 11.6 mmol, 1.1 eq), succinic anhydride (1.15 g, 11.5 mmol, 1.1 eq) and, N,N,N′,N′-tetramethylmethanediamine (1.6 mL, 11.7 mmol, 1.1 eq) and the resulting suspension stirred for 16 hr at 23° C. The reaction was diluted with CH2Cl2 and washed with 20% NaOH (50 mL), water, dried over Na2SO4, and concentrated to afford {5-[4-(tert-Butyl-diphenyl-silanyloxy)-piperidin-1-yl]-imidazo[4,5-b]pyridin-3-ylmethyl}-dimethyl-amine orange oil (5.13 g, 9.89 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ: 7.81 (s, 1H), 7.72 (d, J=6.0 Hz), 4H), 7.42 (m, 6H), 6.67 (d, J=8.6 Hz, 1H), 4.99 (s, 2H), 4.01 (sept, 1H), 3.91 (m, 2H), 3.38 (m, 2H), 2.38 (s, 6H), 1.68-1.78 (m, 4H), 1.10 (s, 9H).

Provenance & Evidence