1-Methylpyrrolidine → HCID 178482686, compound

Participants

Reaction Conditions

Reaction Steps

A solution of prop-1-en-2-yl thiazol-2-ylcarbamate (prepared according to the procedure described in J. Org. Chem. 2005, 70, 6960-6963) (40 mg, 0.054 mmol) and 4-(6-bromo-7-(piperazin-1-yl)-3H-imidazo[4,5-b]pyridin-2-yl)-N,N-dimethylaniline (1.0 eq, 0.054 mmol, 22 mg) in THF (0.5 mL) was heated to 55° C. Then N-methylpyrrolidine (0.1 eq, 0.005 mmol, 5 μL) was added and the mixture stirred at 55° C. for 2 h. Concentration in vacuo gave crude material as a solid. A small sample was purified by semi-preparative hplc to give the pure product as a colourless solid; 1H-NMR (500 MHz, DMSO-d6) 2.99 (s, 6H, N(CH3)2), 3.58-3.62 (m, 4H, piperazine N(CH2)2), 3.74-3.78 (m, 4H, piperazine N(CH2)2), 6.81 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 7.22 (d, J=3.6 Hz, 1H, thiazole H-4 or H-5), 7.35 (br s, 1H, NH), 7.48 (d, J=3.6 Hz, 1H, thiazole H-4 or H-5), 8.02 (d, J=8.9 Hz, 2H, N,N-dimethylaminophenyl), 8.19 (s, 1H, imidazo[4,5-b]pyridine H-5).

Provenance & Evidence