反応 #2286318
ord-6a7de175e06d4513bf59eee6c17ef0ff
反応方程式
反応物
試薬
反応条件
後処理
- 1温度was heated
- 2温度to reflux for 24 h
- 3洗浄washed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL)
- 4抽出extracted with ethyl acetate (50 mL)
- 5乾燥dried over magnesium sulfate
- 6ろ過filtered
- 7濃縮concentrated under vacuum
- 8その他The resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid)
- 9その他The desired fractions were collected
- 10濃縮concentrated
- 11その他freeze dried
- 12その他The resulting solid was purified by flash chromatography
- 13洗浄eluted with 10% methanol in methylene chloride
- 14その他The desired fractions were collected
- 15濃縮concentrated under vacuum
- 16その他to afford a solid which
- 17その他was dried under high vacuum
実験手順
A mixture of [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetonitrile (55) (assume 0.180 mmol) in concentrated hydrochloric acid (4 mL) was heated to reflux for 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (75 mL) and washed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL). The water layers were combined and extracted with ethyl acetate (50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under vacuum. The resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid). The desired fractions were collected, concentrated and freeze dried. The resulting solid was purified by flash chromatography using silica gel eluted with 10% methanol in methylene chloride. The desired fractions were collected and concentrated under vacuum to afford a solid which was dried under high vacuum to afford 3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-acetic acid (56) (8.6 mg, 13% for 2 steps) as a white solid; EI(+)-HRMS m/z calcd for C16H16Cl2N2O3 (M+H)+ 355.0611, found 355.0611. MW=355.2235, Exact Mass=354.0538