HCID 25241964, compound → HCID 59718955, compound

Participants

Reaction Steps

trans-4-Amino-cyclohexanecarboxylic acid methyl ester (727 mg, 3.76 mmol) was added in portions, at RT under nitrogen atmosphere, to a solution of 1-(2,5-dichloro-pyrimidin-4-yl)-1H-benzotriazole (500 mg, 1.88 mmol) in THF (50 mL) followed by TEA (0.79 mL, 5.64 mmol). The resultant white suspension was stirred at RT overnight, and then at 60° C. for 2.5 days. The mixture was partitioned between water (100 mL) and EtOAc (100 mL). The organic layer was separated, washed twice with water (100 mL) and once with brine (100 mL), then dried over Na2SO4, filtered and the solvent evaporated under reduced pressure to give an off-white solid. This crude material was purified via flash chromatography (toluene/EtOAc, 90/10) to afford 538 mg (74% yield) of 4-(4-benzotriazol-1-yl-5-chloro-pyrimidin-2-ylamino)-cyclohexanecarboxylic acid methyl ester as an off-white solid. MS: 387.10 (M+1)+, 359.13 ((M+1)+−28).

Provenance & Evidence