Diisopropylethylamine → (R)-3-(2-{(S)-1-[9-(Tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}benzoimidazol-1-yl)piperidine-1-carboxylic acid tertbutyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-3-[2-((S)-1-aminoethyl)benzoimidazol-1-yl]piperidine-1-carboxylic acid tertbutyl ester (1.65 g, 4.79 mmol), 6-chloro-9-(tetrahydropyran-2-yl)-9H-purine (1.14 g, 4.79 mmol), and DIPEA (2.5 mL, 14.4 mmol) in IMS (10 mL) was stirred in a sealed vial for 48 h at 90° C. After cooling to RT, volatiles were removed under reduced pressure and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in EtOAc). The product containing fractions were concentrated in vacuo affording (R)-3-(2-{(S)-1-[9-(Tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}benzoimidazol-1-yl)piperidine-1-carboxylic acid tertbutyl ester as a white foam (2.27 g, 87%). LCMS: RT 2.88 min [M+H]+ 547.1.

Provenance & Evidence