Sodium Thiosulfate → HCID 178510421, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-cyano-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(4-hydroxymethyl-tetrahydro-pyran-4-yl)-phenyl]-amide (as prepared in Example 20, 75.4 mg, 0.185 mmol), Dess-Martin periodinane (157 mg, 0.369 mmol) and NaHCO3 (155 mg, 1.85 mmol) in 3 mL of DCM was stirred at 0° C. for 0.5 h, at RT for 1 h. To the reaction was added 2 mL of 10% Na2S2O3 and the resulting mixture was stirred vigorously for 5 min. The mixture was treated with 20 mL of H2O and extracted with EtOAc (2×40 mL). The combined organic layers were washed with saturated NaHCO3 aqueous solution (10 mL), H2O (10 mL) and brine (10 mL). After drying over Na2SO4 and concentrating in vacuo, the residue was purified by silica gel chromatography (10-20% EtOAc/DCM) to afford the title compound (45 mg, 60%) as a white solid. Mass spectrum (ESI, m/z): Calcd. for C23H24N4O3, 405.2 (M+H). found 405.1.

Provenance & Evidence