Ethyl diazoacetate → HCID 46200652, compound

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-5-vinyl-pyrazin-2-amine (26 mg, 0.01 mmol) under an atmosphere of nitrogen at room temperature was slowly added a solution of ethyl 2-diazoacetate (34 mg, 31 μL, 0.1 mmol) in toluene (350 μL) over a period of 10 min. The reaction mixture was heated at 110° C. for 1 h. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude material was dissolved in DMSO (1 mL), filtered and purified via reverse phase column chromatography using 10 to 99% MeOH—H2O (TFA modifier) to obtain ethyl 2-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]cyclopropanecarboxylate. 1H NMR (400.0 MHz, CDCl3) δ 8.23-8.15 (m, 3H), 7.59-7.50 (m, 3H), 4.19 (q, J=7.1 Hz, 2H), 2.64 (dd, J=6.2, 12.7 Hz, 1H), 2.25 (dd, J=5.5, 12.4 Hz, 1H), 1.66-1.61 (m, 2H) and 1.39-1.24 (m, 3H) ppm; LC/MS m/z 352.2 [M+H]+.

Provenance & Evidence