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

HRID 2206113노트

반응식

HRID 2206113 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][CH:35]2[CH2:38][O:37][CH2:36]2)(=O)=O)=CC=1>CN(C=O)C>[O:37]1[CH2:38][CH:35]([CH2:34][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)[CH2:36]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 86670828Oxetan-3-ylmethyl 4-methylbenzene-1-sulfonateHCID 1370106734-(4,5-Dihydro-4-oxo-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

생성물 1

HCID 1370107964-(1-(oxetan-3-ylmethyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide수율 15.5%

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 (52.0 mg) obtained in Step B of Example 100 in DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil, 8.60 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added oxetan-3-ylmethyl 4-methylbenzenesulfonate (52.1 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 (10.0 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-9b76dff9a6e641378d6c78d9187ae4d3
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

반응 노트

불러오는 중…