반응 #2286318
ord-6a7de175e06d4513bf59eee6c17ef0ff
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후처리
- 1온도was heated
- 2온도to reflux for 24 h
- 3세척washed with a saturated aqueous sodium chloride solution (20 mL) and water (10 mL)
- 4추출extracted with ethyl acetate (50 mL)
- 5건조dried over magnesium sulfate
- 6여과filtered
- 7농축concentrated under vacuum
- 8기타The resulting oil was purified by HPLC (acetonitrile/water with 0.1% trifluoroacetic acid)
- 9기타The desired fractions were collected
- 10농축concentrated
- 11기타freeze dried
- 12기타The resulting solid was purified by flash chromatography
- 13세척eluted with 10% methanol in methylene chloride
- 14기타The desired fractions were collected
- 15농축concentrated under vacuum
- 16기타to afford a solid which
- 17기타was dried under high vacuum
실험 절차
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