Hydrochloric Acid → 4-(1-(4-hydroxy-4-phenylcyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206174노트

반응식

HRID 2206174 반응식
[O:1]=[C:2]1[C:7]2[C:8]([C:18]3[CH:19]=[C:20]([C:23]([NH2:25])=[O:24])[S:21][CH:22]=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:19]=[C:20]([C:23]([NH2:25])=[O:24])[S:21][CH:22]=3)=[N:9]2)[CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 1370107424-(4-oxo-1-(4-oxocyclohexyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

생성물 1

HCID 1370107004-(1-(4-hydroxy-4-phenylcyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide수율 61.2%

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)thiophene-2-carboxamide (30.0 mg) obtained in Example 170 in THF (10 mL) was added dropwise 1.6 M phenyllithium butyl ether solution (0.210 mL) at −78° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added dropwise 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 (cis/trans mixture, 11.2 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-9300e4d8b8cb42dda30b1977a5e5cdbd
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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