Potassium Carbonate → HCID 66929695, compound

Participants

Reaction Conditions

Reaction Steps

In particular, to a solution of 5-amino-3-[3-(hydroxy)phenylamino]-1-(2-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-6) (0.23 g, 0.75 mmol) in 2-butanone (3 mL) was added K2CO3 (0.11 g, 0.83 mmol) and BrCH2CN (0.10 g, 0.83 mmol). After stirring the mixture at 75° C. for 20 h, the 2-butanone was removed under reduced pressure. The residue was dissolved in EtOAc (50 mL), washed with water (50 mL), brine (30 mL), dried (Na2SO4) and concentrated to afford the crude product. Purification by flash chromatography (1:1 hexanes/EtOAc) gave 5-amino-3-[3-(cyanomethoxy)phenylamino]-1-(2-(methyl)phenyl)carbonyl-1H-1,2,4-triazole (Ia-8) (0.09 g, 35%) as a white solid: Rf 0.29 (1:1 hexanes/ethyl acetate); mp (DSC) 204.5-207.9° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.43 (s, 1H), 7.84 (s, 2H), 7.56 (d, J=7.6 Hz, 1H), 7.46-7.41 (m, 1H), 7.35-7.22 (m, 3H), 7.11 (t, J=8.1 Hz, 1H), 6.96-6.93 (m, 1H), 6.48 (dd, J=8.0, 2.2 Hz, 1H), 4.80 (s, 2H), 2.31 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 168.8, 158.5, 157.0, 156.9, 142.7, 135.5, 134.7, 130.5, 130.4, 129.8, 128.1, 125.5, 116.7, 111.2, 106.3, 103.3, 53.3, 19.5; IR (ATR) 3448, 3368, 2325, 1689 cm−1; APCI MS m/z 349 [C18H16N6O2+H]+; HPLC (Method A) 91.3% (AUC), tR=12.46 min.

Provenance & Evidence