Hydrochloric Acid → HCID 70178460, compound

Participants

Reaction Steps

1-(5-{[tert-Butyl(diphenyl)silyloxy}-2-chlorobenzyl)piperazin-2-one (0.052 g, 0.108 mmol) and N-[1-(4-cyano-3-fluorophenyl)-4-oxo-1-(1-methyl-1H-imidazol-5-yl)butyl]-2-methylpropane-2-sulfinamide (Example 1, Step J) (0.028 g, 0.0.072 mmol)were dissolved in MeOH (5 mL), the pH of the solution adjusted to 5 with HOAc, then NaCNBH3 (0.0068 g, 0.108 mmol) was added. After stirring at ambient temperature for 18 h, the reaction mixture was concentrated in vacuo, partitioned between CH2Cl2 and aqueous saturated NaHCO3 solution, the aqueous layer washed with CH2Cl2 (2×), the organic layers combined and dried (MgSO4). Filtration and concentration in vacuo gave the protected product which was dissolved in MeOH, treated with 4M HCl in dioxane (2 mL), stirred for 1.5 h, concentrated in vacuo, partitioned between CH2Cl2 and aqueous saturated NaHCO3 solution, the aqueous layer washed with CH2Cl2 (2×), the organic layers combined and dried (MgSO4). Filtration and concentration in vacuo, gave the title compound after chromatography on the ISCO Combiflash eluting with 1-5% MeOH/CH2Cl2 with NH4OH. MS(M+1) 749.

Provenance & Evidence