N,N-Diethyl-2-propanamine → (S)-N-(1-([1,2,4]triazolo[4,3-a]pyrazin-8-yl)pyrrolidin-3-yl)-1-phenyl-1H-1,2,4-triazole-3-carboxamide

Participants

Reaction Steps

To a suspension of the above (S)-1-([1,2,4]triazolo[4,3-a]pyrazin-8-yl)pyrrolidin-3-amine hydrochloride salt (90 mg, 0.32 mmol), 1-phenyl-1H-1,2,4-triazole-3-carboxylic acid (58 mg, 0.30 mmol) in DMF (5 mL) was added diethylisopropyl amine (650 mg, 5 mmol), followed by HATU (120 mg, 0.31 mmol). The resulting solution was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous solutions of KH2PO4 and NaHCO3, followed by brine. The organic layer was concentrated in vacuo and the residue purified by reverse phase HPLC (acetonitrile-H2O with 0.1% TFA as eluent) to give 23 mg of the title compound (20% yield) as white solid. 1H NMR (400 MHz, d6-DMSO) δ 2.10-2.38 (two sets of m, 2 H), 3.50-4.60 (br, 4 H), 4.65 (m, 1 H), 7.29 (d, J=4.4 Hz, 1 H), 7.46 (t, J=7.3 Hz, 1 H), 7.59 (t, J=7.3 Hz, 2 H), 7.75 (d, J=4.7 Hz, 1 H), 7.90 (d, J=8.0 Hz, 2 H), 9.00 (d, J=7.0H, 1 H), 9.20 (s, 1 H), 9.40 (s, 1 H). MS: (ES) m/z calculated for C18H17N9O [M+H]+ 376.2, found 376.2.

Provenance & Evidence