Ethyl orthoformate → HCID 178455732, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 2,6-dichloro-N3-(1-(trans-4-methylcyclohexyl)ethyl)pyridine-3,4-diamine (35 g, 0.116 mol) in triethylorthoformate (200 mL, 1.16 mol) was stirred at 100° C. for 3 h. TLC (petroleum ether/ethyl acetate=3/1) showed the reaction was complete. The solvent was removed under reduced pressure. The residue was purified by column chromatography (petroleum ether/ethyl acetate=10:1) to give the crude product, which was washed with a mixture of petroleum ether/ethyl acetate=10:1 to afford 4,6-dichloro-3-[1-(trans-4-methylcyclohexyl)ethyl]-3H-imidazo[4,5-c]pyridine. 1H NMR (400 MHz, DMSO-d6) δ: 8.85 (s, 1H), 7.86 (s, 1H), 4.98 (bs, 1H), 1.76-1.67 (m, 3H), 1.58-1.56 (m, 4H), 1.23-1.20 (m, 2H), 1.07-0.99 (m, 2H), 0.84-0.79 (m, 5H). MS ESI calc'd. for C15H19Cl2N3 [M+H]+ 312. found 312.

Provenance & Evidence