Triethylamine → HCID 58997363, compound

Participants

Reaction Steps

Combine triethylamine (15.8 mL, 111.0 mmol) and 2,6-diaminopyridine (6.5 g, 59.6 mmol) in dioxane (200 mL). Add 4-fluorobenzoyl chloride (5.46 mL, 44.7 mmol) in small increments. After complete addition, stir at room temperature for 18 hr. Pour into water and dilute with ethyl acetate and water. Separate and extract twice the aqueous layer with CH2Cl2, combine the organic fractions, dry over MgSO4, and concentrate. Chromatograph on silica gel, eluting with a gradient of 0%–10% (2M NH3 in methanol) in CH2Cl2 to give the title intermediate (8.91 g, 86.3%): mass spectrum (ion spray): m/z=232.3 (M+1); Analysis calc'd for C12H10N3OF.0.1H2O: C, 61.85; H, 4.41; N, 18.03. Found: C, 61.75; H, 4.08; N, 17.66.

Provenance & Evidence