Acetic Acid → HCID 66938955, compound

Participants

Reaction Steps

Combine 4-cyanobenzoyl chloride (300 μL, 1.80 mmol), 2,6-diaminopyridine (600 mg, 5.5 mmol, and dioxane (10 mL); stir at room temperature for 2 hr. Pour into water and adjust to pH>12 by the addition of 5N NaOH. Extract with CH2Cl2 twice, combine organics, dry over MgSO4, and concentrate. Chromatograph (silica gel, eluting with 0–10% methanol/CH2Cl2). Dissolve the purified intermediate N-(6-amino-pyridin-2-yl)-4-cyano-benzamide (202 mg, 0.84 mmol, 47%) in THF (10 mL). Add to this 1-methyl-4-piperidone (77 mg, 0.68 mmol), acetic acid (150 μL, 2.5 mmol), and sodium triacetoxyborohydride (440 mg, 2.10 mmol). Stir the reaction at room temperature for 18 hr, and quench by the addition of saturated aqueous NaHCO3. Extract the aqueous layer with ethylacetate twice, wash the combined organics with saturated aqueous NaCl, dry over MgSO4, and concentrate. Chromatograph the material (silica gel, eluting with 0–20% 2M NH3 in methanol/CH2Cl2). Dissolve the clean material (10.4 mg, 5%) in methanol and add 1 equivalent (1.7 mg) of NH4Cl. Sonicate the reaction at room temperature for 15 min, then concentrate to provide the title compound: mass spectrum (ion spray): m/z=336.0 (M+1).

Provenance & Evidence