Ammonium Chloride → HCID 67280019, compound

Participants

Reaction Steps

A mixture composed of {4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}acetic acid of Example 111 (24 mg), dimethylformamide (0.7 ml), ammonium chloride (13 mg), 1-hydroxybenzotriazole monohydrate (6 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (15 mg) and diisopropylethylamine (34 μl) was stirred at room temperature for three days. The solvent in the reaction mixture was evaporated by spraying, and a 0.2 N sodium hydroxide solution was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was concentrated under reduced pressure. Dichloromethane (2 ml) and trifluoroacetic acid (0.5 ml) were added to the resulting residue, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was placed into the resulting residue, followed by extraction with chloroform. The organic layer was dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (16.1 mg, 70%) as a solid.

Provenance & Evidence