Triethylamine → HCID 18974970, compound

Participants

Reaction Steps

4-(4-Aminobenzyl)-6-(4-chlorophenyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene (24.8 mg) obtained in Example 188 was dissolved in dichloromethane (2 ml) and triethylamine (30 μl) was added. The mixture was ice-cooled and methanesulfonyl chloride (7 μl) was added. The mixture was stirred under ice-cooling for 10 minutes and at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and a 5% aqueous citric acid solution and ethyl acetate were added. The organic layer, was separated, and successively washed with a saturated aqueous sodium hydrogencarbonate solution and water. The organic layer was dried, filtered and concentrated under reduced pressure. The residue obtained was separated and purified by preparative thin-layer chromatography. Both compounds were individually crystallized from ethyl acetate-diethyl ether to give 8 mg of 6-(4-chlorophenyl)-4-(4-methylsulfonylaminobenzyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene (m.p. 273°-275° C.) and 16 mg of 4-[4-bis(methylsulfonyl)aminobenzyl]-6-(4-chlorophenyl)-4H-2,3,4,5,10b-pentaazabenz[e]azulene (m.p. 220°-221° C.).

Provenance & Evidence