Oxalyl chloride → HCID 178501265, compound

Participants

Reaction Steps

0.350 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (1.26 mmol, 1 eq.) is placed in 13 mL of dichloromethane with stirring, at room temperature, under a nitrogen atmosphere. 0.16 mL of oxalyl chloride (1.89 mmol, 1.5 eq.) and 2 drops of dimethylformamide are successively added. The reaction medium is stirred for 1.5 hours and concentrated under vacuum. The methyl cis-4-(4-chlorocarbonylphenoxy)cyclohexanecarboxylate formed is dissolved in 13 mL of acetonitrile and placed under nitrogen. 0.255 g N-cyclopentyl[1.3.4]thiadiazole-2,5-diamine (1.39 mmol, 1.1 eq.) and 0.12 mL of pyridine (1.51 mmol, 1.2 eq.) are successively added. After 3 days, the medium is filtered and rinsed with acetonitrile to give 0.33 g of methyl cis-4-[4-(5-cyclopentylamino[1.3.4]thiadiazol-2-ylcarbamoyl)phenoxy]cyclohexanecarboxylate.

Provenance & Evidence