Pyridine → HCID 18327313, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.), stirred solution of 5-(2-fluorophenyl)-3-phenylsulfenylmethyl-3H-1,2,3-triazol-4-ylamine (1 g, 3.33 mmol) in dimethylformamide (15 ml) was added pyridine (460μl, 4.33 mmol) followed by 2-chloro-2-cyclobutylacetyl chloride (810 mg, 3.83 mmol) and the reaction stirred at 0° C. for 1 hour. The reaction was quenched by partitioning between ethyl acetate (100 ml) and water (100 ml). The layers were separated and the aqueous layer extracted with ethyl acetate (100 ml). The combined organic extracts were washed with citric acid (50 ml, 10% aqueous), sodium bicarbonate (50 ml, sat. aqueous), brine (50 ml). dried (Na2SO4) and the solvent removed in vacuo. The crude product was purified by flash chromatography (40% EtOAc/hexanes) to afford 2-chloro-2-cyclobutyl-N-[5-(2-fluorophenyl)-3-phenylsulfenylmethyl-3H-1,2,3-triazol-4-yl]acetamide (450 g, 31%; 52% based on recovered starting material) as a crystalline solid, m.p. 103-104° C.; δH (400 MHz, CDCl3) 1.79-2.18 (6H, m, CH(CH2)3), 2.83-2.93 (1H, m, CH(CH2)3), 4.28 (1H, d, J=8 Hz, CHCl), 5.58 (1H, d, J=14.3 Hz, PhSCH2A), 5.64 (1H, d, J=14.3 Hz, PhSCH2B), 7.10-7.16 (1H, m, ArH), 7.23-7.41 (7H, m, ArH), 7.79-7.85 (1H, m, ArH), 8.00-8.10 (1H, br m, NH); m/z (ES+) 431 (100%) (35ClM+H+), 433 (40%) (37 ClM+H+).

Provenance & Evidence