Acetic Acid → Acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester

HRID 1157229노트

반응식

HRID 1157229 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][OH:22])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[N:10]=[N:11][C:12](Cl)=[C:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=1.[C:23]([O-])(=[O:25])[CH3:24].[Na+].C(O)(=[O:30])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:20][CH2:21][O:22][C:23](=[O:25])[CH3:24])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[C:13]([CH:15]([CH3:17])[CH3:16])[C:12](=[O:30])[NH:11][N:10]=1

참가 물질

4

반응물 3

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 598345252-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol

생성물 1

HCID 59834524Acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester수율 100%

반응 조건

온도
114 °C

실험 절차

A solution of 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-ethanol (17) (500 mg, 1.38 mmol) in glacial acetic acid (5 mL) was treated with sodium acetate (230 mg, 2.8 mmol) and heated to 114° C. for 24 h. At this time, the reaction mixture was cooled to room temperature and was concentrated under vacuum. The resulting residue was diluted with methylene chloride (25 mL) and was washed with water (10 mL). The organic layer was separated and was washed with a saturated aqueous sodium bicarbonate solution (10 mL). The waters layers were combined and extracted with methylene chloride (10 mL). The organic layers were combined and dried with sodium sulfate, filtered, concentrated and dried under high vacuum overnight to afford acetic acid 2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-ethyl ester (34) (531 mg, 100%) as a white solid; LRMS for C17H18Cl2N2O4 (M+) m/z=385 Molecular Weight=385.2500; Exact Mass=384.0644

후처리

  1. temperatureAt this time, the reaction mixture was cooled to room temperature
  2. concentrationwas concentrated under vacuum
  3. additionThe resulting residue was diluted with methylene chloride (25 mL)
  4. washwas washed with water (10 mL)
  5. customThe organic layer was separated
  6. washwas washed with a saturated aqueous sodium bicarbonate solution (10 mL)
  7. extractionextracted with methylene chloride (10 mL)
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried under high vacuum overnight

출처 및 근거

ORD 기록
ord-5653e9ce0ee44a809c201560bcdd6e64
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807674B2

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