Diisopropylethylamine → 2-(5-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-ylamino)-acetonitrile

Participants

Reaction Steps

To a solution of 5-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2(3H)-one (350 mg, in about 60% pure) in DMF (4 mL) at RT was sequentially added 2-aminoacetonitrile hydrochloride (302 mg, 3.27 mmol) (Alfa Aesar), diisopropylethylamine (0.79 mL, 4.57 mmol) and BOP (530 mg, 1.20 mmol) (Aldrich). After the reaction was stirred at RT for 18 h, it was diluted with H2O (10 mL) and extracted with EtOAc (3×25 mL). The aqueous layer was discarded. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified on a silica gel column eluting with 25-100% EtOAc in Hex to give 2-(5-(3-(4-isopropylpyrimidin-2-yl)-1H-indol-5-yl)-1,3,4-oxadiazol-2-ylamino)-acetonitrile (45 mg) as a brown amorphous solid. MS (ESI, pos. ion) m/z: 360.0 (M+1). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.99 (1H, br.), 9.16 (1H, s), 8.69 (1H, d, J=5.1 Hz), 8.49 (1H, t, J=5.7 Hz), 8.33 (1H, m), 7.73 (1H, d, J=8.2 Hz), 7.62 (1H, d, J=8.6 Hz), 7.16 (1H, d, J=5.1 Hz), 4.43 (2H, d, J=5.7 Hz), 3.06 (1H, dt, J=13.7, 6.8 Hz), 1.37 (6H, d, J=6.8 Hz).

Provenance & Evidence