Sodium Thiosulfate → 6,6-Dimethyl-11-oxo-8-(4-oxo-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 2275115

반응식

HRID 2275115 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:23](=[O:24])[C:22]4[C:21]5[C:16](=[CH:17][C:18]([C:25]#[N:26])=[CH:19][CH:20]=5)[NH:15][C:14]=4[C:13]([CH3:28])([CH3:27])[C:12]=3[CH:29]=2)[CH2:4][CH2:3]1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+].COC1CCCC1>C(Cl)Cl.CN(C=O)C>[CH3:27][C:13]1([CH3:28])[C:14]2[NH:15][C:16]3[C:21](=[CH:20][CH:19]=[C:18]([C:25]#[N:26])[CH:17]=3)[C:22]=2[C:23](=[O:24])[C:11]2[CH:10]=[CH:9][C:8]([N:5]3[CH2:6][CH2:7][C:2](=[O:1])[CH2:3][CH2:4]3)=[CH:29][C:12]1=2

참가 물질

7

반응물 4

HCID 24477Sodium ThiosulfateHCID 138539Cyclopentyl methyl etherHCID 516892Sodium BicarbonateHCID 545808688-(4-hydroxypiperidin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

생성물 1

HCID 668341076,6-Dimethyl-11-oxo-8-(4-oxo-piperidin-1-yl)-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

8-(4-Hydroxy-piperidin-1-yl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound B2-7-1, 210 mg, 0.545 mmol), was dissolved in the DCM (2 mL) and DMF (0.6 mL) mixture solvent, added with 1,1,1-triacetoxy-1,1-dihydro-1,2-benzoiodoxol-3(1H)-one (300 mg, 1.3 eq.), and the mixture was stirred at room temperature for 2 hr. To the reaction solution, 0.25 mol/L aqueous solution of sodium thiosulfate, saturated sodium bicarbonate solution and CPME were added followed by further stirring at room temperature for 1 hr. The reaction solution was filtered and the filtrate was subjected to liquid separation. The organic layer was washed with saturated brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the target compound (yellowish white powder, 109 mg, 52%).

후처리

  1. stirringby further stirring at room temperature for 1 hr
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate was subjected to liquid separation
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe drying agent was removed by filtration
  7. customthe residues obtained
  8. concentrationafter concentration under reduced pressure
  9. customwere purified by silica gel column chromatography (ethyl acetate/hexane)
  10. customto obtain the target compound (yellowish white powder, 109 mg, 52%)

출처 및 근거

ORD 기록
ord-5475db352ffc49c999b236e18887603f
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126931B2

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