N-methyl-2-pyrrolidone → 3-Quinolin-6-ylmethyl-imidazo[1,2-b]pyridazine-6-carbonitrile

반응식

Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[CH:9][N:10]=2)[N:7]=1.[C:21]([Cu])#[N:22].[CH3:24]N1C(=O)CCC1>CCOC(C)=O>[N:12]1[C:13]2[C:14](=[CH:24][C:20]([CH2:11][C:8]3[N:6]4[N:7]=[C:2]([C:21]#[N:22])[CH:3]=[CH:4][C:5]4=[N:10][CH:9]=3)=[CH:19][CH:18]=2)[CH:15]=[CH:16][CH:17]=1

참가 물질

실험 절차

(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-quinoline (Example 14) (50 mg, 0.17 mmol) and CuCN (23 mg, 0.26 mmol) in 0.5 mL NMP were heated under microwave irradiation at 230° C. for 9.5 h. The RM was diluted with EtOAc and washed with aqueous saturated NaHCO3 and brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by preparative HPLC with acetonitrile and water (+0.1% TFA) to yield the title compound as a yellow solid (tR 2.16 min (conditions 8), MH+=286).