N,N-Dimethylformamide--water (1/1) → HCID 58447743, compound

Participants

Reaction Conditions

Reaction Steps

To a sealed tube were added N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(3-chloro-2′-methyl-2,4′-bipyridin-5-yl)acetamide 184 (46 mg, 0.10 mmol), zinc cyanide (14 mg, 0.12 mmol), Pd2(dba)3 (9 mg, 0.010 mmol), Q-phos (9 mg, 0.022 mmol) and 1 ml DMF/H2O (99/1, v/v). The reaction mixture was bubbled with nitrogen for 1 minute and stirred at 130° C. overnight. After cooling to room temperature, the solvents were evaporated and the crude product was purified by reverse phase HPLC to give N-(5-(4-acetylpiperazin-1-yl)pyridin-2-yl)-2-(3-cyano-2′-methyl-2,4′-bipyridin-5-yl)acetamide 188. MS m/z 456.2 (M+1); 1H NMR 400 MHz (MeOD) δ 8.85(d, 1H), 8.56(d, 1H), 8.28(d, 1H), 7.98(s, 1 Hz), 7.88(d, 1H), 7.78(s, 1H), 7.73-7.70(m, 1 Hz), 7.39(dd, 1H), 3.89(s, 2H), 3.69(t, 2H), 3.65(t, 2H), 3.16(t, 2H), 3.11(t, 2H), 2.61(s, 3H), 2.09(s, 3H).

Provenance & Evidence