反应 #2286318
ord-6a7de175e06d4513bf59eee6c17ef0ff
反应方程式
反应物
试剂
反应条件
后处理
- 1温度was heated
- 2温度to reflux for 24 h
- 3洗涤washed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL)
- 4萃取extracted with ethyl acetate (50 mL)
- 5干燥dried over magnesium sulfate
- 6过滤filtered
- 7浓缩concentrated under vacuum
- 8其他The resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid)
- 9其他The desired fractions were collected
- 10浓缩concentrated
- 11其他freeze dried
- 12其他The resulting solid was purified by flash chromatography
- 13洗涤eluted with 10% methanol in methylene chloride
- 14其他The desired fractions were collected
- 15浓缩concentrated under vacuum
- 16其他to afford a solid which
- 17其他was dried under high vacuum
实验过程
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