Hydrochloric Acid → 4-(1-(4-hydroxy-4-phenylcyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

HRID 2206177노트

반응식

HRID 2206177 반응식
[O:1]=[C:2]1[C:7]2[C:8]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]3)[C:6]=2[CH:5]=[CH:4][NH:3]1.Cl>C1COCC1>[OH:17][C:14]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:13][CH2:12][CH:11]([N:10]2[C:6]3[CH:5]=[CH:4][NH:3][C:2](=[O:1])[C:7]=3[C:8]([C:18]3[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)=[N:9]2)[CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 1370106124-(4-oxo-1-(4-oxocyclohexyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

생성물 1

HCID 1370105954-(1-(4-hydroxy-4-phenylcyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide수율 83.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(4-oxo-1-(4-oxocyclohexyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (30.0 mg) obtained in Example 173 in THF was added 1.6M phenyllithium butyl ether solution (0.194 mL) at −78° C., and the mixture was stirred overnight at room temperature under nitrogen atmosphere. To the reaction mixture was added 1N hydrochloric acid at 0° C., and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (15.1 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-f095e42554044be4bb32dd60547d8321
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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