Pyridine → HCID 58754879, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 24.0 mg (0.0785 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylate potassium salt (as prepared in Example 11, step (d)) in CH2Cl2 (5 mL) was treated with 6.40 μL (0.0785 mmol) of pyridine for 5 min. The mixture was cooled to 0° C., and 5.70 μL (0.0785 mmol) of SOCl2 was added, allowed to warm to RT, and stirred for 30 min. A solution of 20.0 mg (0.0620 mmol) of 2-cyclohex-1-enyl-4-(morpholine-4-sulfonyl)-phenylamine (as prepared in the previous step) and triethylamine (12.0 μL, 0.0854 mmol) in CH2Cl2 (1 mL) was treated with the acid chloride solution and stirred at RT for 7 h. The mixture was diluted with CH2Cl2 (10 mL) and washed with water (1×10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 15.0 mg (37%) of the title compound as a tan solid: Mass spectrum (ESI, m/z): Calcd. for C27H37N5O5SSi, 572.2 (M+H), found 572.0.

Provenance & Evidence