Multi-step reaction with 8 steps
1: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight
2: 4 N HCl / dioxane / 1 h / Ambient temperature
3: 1.) hydroxybenzotriazole (HOBt), EDCI, 2.) N-methylmorpholine (NMM) / 1.) DMF, 40 min, 2.) DMF, a) 0 deg C, 2 h, b) RT, overnight
4: 4 N HCl / dioxane / 1 h / Ambient temperature
5: triethylamine, DCM / dimethylformamide / 2 h / 0 - 20 °C
6: NaI, NaHCO3 / dimethylformamide / 18 h / Ambient temperature
7: NaBH4 / methanol
8: 99 percent / H2 / 10percent Pd(OH)2/C / aq. acetic acid / 4 h
With
4-methyl-morpholine; hydrogenchloride; sodium tetrahydroborate; hydrogen; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; sodium hydrogencarbonate; benzotriazol-1-ol; triethylamine; sodium iodide;
palladium dihydroxide;
In
1,4-dioxane; methanol; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jm00099a008