Triethylamine → HCID 12150105, compound

Participants

Reaction Steps

95 mg (0.24 mmol) of 4-[3-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalene-1-carboxylic acid (Example 17) was dissolved in 1 mL of DMF. To this clear solution was added sequentially, 139 mg (0.44 mmol) of TBTU, and 102 microL (0.73 mmol) of triethylamine. The clear yellow solution was stirred for 5 min, then 50 mg (0.31 mmol) of morpholin-2-yl-acetic acid methyl ester (Loftus, F. Syn. Commun. 1980, 10, 59) was added. The reaction was stirred overnight, then concentrated in vacuo. The resulting amber oil was extracted with EtOAc and water, brine, and then dried over magnesium sulfate. Concentration in vacuo provide an amber oil which was purified on silica gel, eluting with 5% MeOH-methylene chloride to provide 93 mg (72%) of the title compound as a viscous oil.

Provenance & Evidence