Triethylamine → HCID 19047185, compound

Participants

Reaction Conditions

Reaction Steps

2.0 g (0.0073 mol) of the title compound of Step D of Example 1 was added to 50 mL of methylene chloride. 1.27 mL (0.0146 mol) of oxalyl chloride (purchased from Janssen) was added followed by 2 drops of N,N-dimethylformamide. The mixture was refluxed under nitrogen for 2 h and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and evaporated to dryness. Another 50 mL of methylene chloride was added to the residue and the solution was cooled to about 0° C. 0.90 g (0.0080 mol) of 1-ethyl-1H-pyrazol-5-ol was added to the mixture followed by 2.8 mL (0.0020 mol) of triethylamine and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness. The residue was stirred in 100 mL of water and the water was decanted. The residue was washed with hexane (2×100 mL) and then chromatographed on silica gel eluting with 4:6 ethyl acetate/hexane to yield 1.57 g of the title compound of Step A as a solid melting at 119°-120° C. 1H NMR (CDCl3): δ 1.4 (t, 3H), 1.5 (s, 6H), 2.5 (m, 2H), 2.8 (s, 3H), 3.4 (m, 2H), 4.1 (q, 2H), 6.2 (d, 1H), 7.5 (d, 1H).

Provenance & Evidence