Ammonium Chloride → 4-(1-(4-hydroxycyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

HRID 2206173노트

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HRID 2206173 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.[BH4-].[Na+].[Cl-].[NH4+]>CO>[OH:17][CH:14]1[CH2:15][CH2:16][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)[CH2:12][CH2:13]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 1370107424-(4-oxo-1-(4-oxocyclohexyl)-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide

생성물 1

HCID 1370106254-(1-(4-hydroxycyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)thiophene-2-carboxamide수율 76.8%

시약·촉매·용매 1

HCID 887Methanol용매

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 (40.0 mg) obtained in Example 170 in methanol (5 mL) was added sodium borohydride (8.49 mg) at 0° C., and the mixture was stirred overnight under nitrogen atmosphere at room temperature. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. 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 (cis/trans mixture, 30.9 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 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 (basic silica gel, ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-5f1c2160ab134c61ad71e2d98f82a926
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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