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Hydrochloric Acid → 8-(2-Hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one

HRID 1039010
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HRID 1039010 반응식
C[O:2][C:3]1[C:8]([N:9]2[CH2:30][CH2:29][C:12]3([C:16](=[O:17])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=4)[CH2:14][CH2:13]3)[CH2:11][CH2:10]2)=[CH:7][CH:6]=[CH:5][N:4]=1.[Na+].[I-].C[Si](Cl)(C)C.Cl.S(=O)(O)[O-].[Na+]>C(#N)C.[Cl-].[Na+].O.CCOC(C)=O>[OH:2][C:3]1[C:8]([N:9]2[CH2:10][CH2:11][C:12]3([C:16](=[O:17])[N:15]([C:18]4[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:28])[F:26])=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)[CH2:29][CH2:30]2)=[CH:7][CH:6]=[CH:5][N:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 23665763Sodium BisulfiteHCID 56655687HCID 56655687, 화합물

생성물 1

HCID 1785172998-(2-Hydroxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one수율 65%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 8-(2-methoxy-pyridin-3-yl)-2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (described in example 9, 40 mg, 0.095 mmol) in acetonitrile (2 mL) at 0° C. was added NaI (28.5 mg, 0.19 mmol). TMSCl (24 uL, 0.19 mmol) was added, and the mixture was stirred and allowed to warm to rt over overnight. 1N Hydrochloric acid (1 mL), 38% aqueous sodium bisulfite solution (0.5 mL), brine and EtOAc (10 mL) were added, and the mixture was stirred for 30 min. The phases were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic phases were washed with sat. NaHCO3, brine, dried (Na2SO4), filtered and evaporated under reduced pressure to yield the title compound as a light green solid (25 mg, 65%). MS (ESI): 408.3 (MH+).

후처리

  1. stirringthe mixture was stirred for 30 min
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional EtOAc
  4. washThe combined organic phases were washed with sat. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-e031abb4cb9a4299aac34595feaa2236
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552024B2

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