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

HRID 2206129노트

반응식

HRID 2206129 반응식
[Si]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:23]3[CH:22]=[CH:21][N:20]=[C:19]([O:24]C)[C:18]=3[C:17]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[OH:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[C:23]3[CH:22]=[CH:21][NH:20][C:19](=[O:24])[C:18]=3[C:17]([C:26]3[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=3)=[N:16]2)[CH2:11][CH2:10]1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 1317358374-(1-(4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide

생성물 1

HCID 1370106494-(1-(4-hydroxycyclohexyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide수율 76.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of 4-(1-(4-((tert-butyl(dimethyl)silyl)oxy)cyclohexyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzenesulfonamide (42.8 mg) obtained in Step A of Example 119 in acetonitrile (3 mL) were added sodium iodide (31.0 mg) and chloro(trimethyl)silane (0.105 mL), and the mixture was stirred at 50° C. for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (24.6 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 sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-452cc626f07349cfb5d9d66f7bb420ce
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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