Triethylamine → HCID 58080690, compound

Participants

Reaction Steps

Compound X (0.10 g, 1.0 eq) was taken up in N,N-dimethylacetamide (2 ml) then treated with HBTU (0.16 g, 1.3 eq) and triethylamine (49 uL, 1.1 eq). After 10 minutes at room temperature, commercially available 4-aminomethylpyridine (37.8 mg, 1.1 eq) was added. The reaction stirred at room temperature for 15 h before diluting with saturated NH4Cl aq. to quench. The mixture was extracted with ethylacetate (3×-5 ml). The organics were washed with water (3×-5 mL), and brine (2×-5 mL) then dried over Na2SO4 and concentrated for crude material. The residue was loaded on silica gel (24 g) and eluted with a gradient of 0-10 MeOH/DCM for 20 CVs. Late fractions afforded the desired product as a lightly tan solid (5.1 mg, 3.8% yield; calc M+H 402, obs M+H 402).

Provenance & Evidence