Triethylamine → HCID 178464464, compound

Participants

Reaction Steps

A solution of 0.15 g (0.44 mmol) of trans-4-{2-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-ethyl}-cyclohexanecarboxylic acid in 4 mL of CH2Cl2 was treated at RT with 1 drop of DMF, followed by 0.04 mL (0.48 mmol, 1.1 eq) of oxalyl chloride within 5 min, and stirring was continued for 90 min. The solution was then evaporated, the residue redissolved in acetonitrile and added dropwise to a solution of 0.29 g (1.32 mmol, 3 eq) of 2-[ethyl-(2-methylamino-ethyl)-amino]-ethanol•2HCl and 0.92 mL (6.57 mmol) of Et3N in 4 mL of DMA at 0° C. The reaction was warmed to RT and left overnight, then partitioned between Et2O(×3)/aqueous 10% NaHCO3(2×), dried over Na2SO4 and evaporated then chromatographed over silica gel (20 g) prepared in CH2Cl2:MeOH 97.5:2.5 and eluted in 95:5 to yield 0.13 g (64%) of pure trans-4-{2-[(5-bromo-pyrimidin-2-yl)-methyl-amino]-ethyl}-cyclohexanecarboxylic acid {2-[ethyl-(2-hydroxy-ethyl)-amino]-ethyl}-methyl-amide, MS: 470 (MH+, 1Br).

Provenance & Evidence