Sodium hydride → 4-(1-((3-methyloxetan-3-yl)methyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

HRID 2206104노트

반응식

HRID 2206104 반응식
[O:1]=[C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[N:9][NH:10][C:6]=2[CH:5]=[CH:4][NH:3]1.[H-].[Na+].CC1C=CC(S(O[CH2:34][C:35]2([CH3:39])[CH2:38][O:37][CH2:36]2)(=O)=O)=CC=1>CN(C=O)C>[CH3:34][C:35]1([CH2:39][N:10]2[C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=3[C:8]([C:11]3[CH:12]=[CH:13][C:14]([S:17]([NH2:20])(=[O:19])=[O:18])=[CH:15][CH:16]=3)=[N:9]2)[CH2:38][O:37][CH2:36]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 5461213(3-Methyloxetan-3-yl)methyl 4-methylbenzenesulfonateHCID 1370106734-(4,5-Dihydro-4-oxo-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

생성물 1

HCID 1370105844-(1-((3-methyloxetan-3-yl)methyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide수율 31.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-(4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (34.5 mg) in DMF (2 mL) was added sodium hydride (60% dispersion in mineral oil, 7.13 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added (3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (45.7 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was extracted with water and ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol) to give the title compound (14.2 mg).

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionThe reaction mixture was extracted with water and ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-bab58668130f4b19bd13750dd5edbae7
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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