Diisopropylethylamine → HCID 91104069, compound

Participants

Reaction Steps

To 5-(aminomethyl)-1-(4-cyano-3-fluorobenzyl)imidazole hydrochloride, as described above in Step B, (54 mg, 0.18 mmol) in dry THF (2 mL) under argon were added PYBOP (219 g, 0.42 mmol), N-[7-(triisopropylsilyloxy)naphthalene-1-carbonyl]glycine lithium salt, as described above in Step D, (171 mg, 0.42 mmol), and N,N-diisopropylethylamine (0.124 mL, 0.71 mmol). The reaction mixture was stirred for 3 hrs, then partitioned between CH2Cl2 (30 mL) and saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted further with CH2Cl2 (2×15 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with a gradient of CH2Cl2-1% MeOH −0.1% NH4OH to CH2Cl2-5% MeOH −0.5% NH4OH, to yield the desired product as a pale foam.

Provenance & Evidence