Acetyl chloride → HCID 24992764, compound

Participants

Reaction Steps

To 6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-carboxylic acid prepared in similar fashion to the product of Example 124 Step B (20 mg, 0.05 mmol) in MeCN (1 mL) was added 1-hydroxybenzotriazole (HOBt) (7 mg, 0.005 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarboddimide hydrochloride (EDAC) (10 mg, 0.05 mmol) and the reaction was stirred at rt for 30 min. The reaction was cooled to 0° C. and hydrazine hydrate (0.005 mL, 0.09 mmol) was added and the reaction was stirred for 5 min. EtOAc was added and the organic portion was washed with saturated aq NaHCO3 and water, dried (Na2SO4), filtered and concentrated. The residue was dissolved in CH2Cl2 (2 mL). Acetyl chloride (0.025 mL, 0.35 mmol) was added and the reaction was stirred 10 min. EtOAc was added and the solution was washed with saturated aq NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was dissolved in toluene (0.5 mL) and POCl3 (0.2 mL) was added. The reaction was refluxed overnight, diluted with CH2Cl2, washed with a saturated aq solution of NaHCO3, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0-50% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 500.2 (M+1), 502.2 (M+3); Rt=3.91 min.

Provenance & Evidence