Water → 6'-[Acetyl-(3-chloro-benzyl)-amino]-2,3,5,6-tetra-hydro-[1,2']bipyrazinyl-4-carboxylic acid tert-butyl ester

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Reaction Steps

To a solution of 6′-acetylamino-2,3,5,6-tetrahydro-[1,2′]bipyrazinyl-4-carboxylic acid tert-butyl ester I-5b (36.9 mg, 0.11 mmol) and 1-bromomethyl-3-chloro-benzene (15.8 μL, 0.12 mmol) in DMF (1.1 mL) at room temperature was added 60% NaH in mineral oil (5 mg, 0.13 mmol). After stirring at room temperature for 4 h, the reaction mixture was poured into H2O (10 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with H2O (3×10 mL), brine, dried (Na2SO4), filtered, and evaporated to dryness. The crude material was purified by preparative TLC using 50% ethyl acetate/ether with 1% NH4OH to afford the title compound I-5c (27.1 mg).

Provenance & Evidence