Triethylamine → 2-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one

HRID 2249410노트

반응식

HRID 2249410 반응식
[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][OH:13])=[CH:8][C:7]([C:14]3[CH:15]=[CH:16][C:17]4[O:21][CH2:20][CH2:19][C:18]=4[CH:22]=3)=[N:6]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH:1]1([CH2:4][N:5]2[C:10](=[O:11])[C:9]([CH2:12][O:13][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:8][C:7]([C:14]3[CH:15]=[CH:16][C:17]4[O:21][CH2:20][CH2:19][C:18]=4[CH:22]=3)=[N:6]2)[CH2:3][CH2:2]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 230941232-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-hydroxymethyl-2H-pyridazin-3-one

생성물 1

HCID 230941212-cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-methanesulfonyloxymethyl-2H-pyridazin-3-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-Cyclopropylmethyl-6-(2,3-dihydro-1-benzofuran-5-yl)-4-hydroxymethyl-2H-pyridazin-3-one (540 mg, 1.81 mmol) was dissolved in methylene chloride (12 mL), and triethylamine (238 mg, 2.35 mmol) and methanesulfonyl chloride (249 mg, 2.17 mmol) were added to the solution under cooling with ice, followed by stirring for one hour. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate anhydrate. The solvent was removed under reduced pressure, and the residue was recrystallized from chloroform-hexane, to thereby yield 607 mg of the title compound as a pale yellow crystalline powder (89.1%).

후처리

  1. temperatureunder cooling with ice
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was recrystallized from chloroform-hexane

출처 및 근거

ORD 기록
ord-f055003059be4a33aaf03e5de6bc8249
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07314877B2

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