Dimethyl Sulfoxide → HCID 68006252, compound

HRID 1026606Notes

Reaction equation

HRID 1026606 reaction equation
CS(C)=O.Br[CH:6]1[C:15]2[C:10](=[CH:11][C:12]([Cl:16])=[CH:13][N:14]=2)[N:9]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)[C:8](=[O:30])[C:7]1([CH3:32])[CH3:31].C(=O)([O-])[OH:34].[Na+]>O>[Cl:16][C:12]1[CH:11]=[C:10]2[C:15]([C:6](=[O:34])[C:7]([CH3:32])([CH3:31])[C:8](=[O:30])[N:9]2[CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[N:14][CH:13]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 516892Sodium BicarbonateHCID 68006085HCID 68006085, compound

Product 1

HCID 68006252HCID 68006252, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a dimethylsulfoxide solution (8 ml) of tert-butyl 4-(4-bromo-7-chloro-3,3-dimethyl-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (375 mg) was added sodium hydrogen carbonate (871 mg), followed by stirring at 100° C. for 6 hours. Water was added to the reaction solution, and extracted with ethyl acetate. The collected organic layer was washed sequentially with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. After the resulting residue was dissolved in dichloromethane (14 ml), manganese dioxide (684 mg) was added and stirred for 50 minutes, and further manganese dioxide (690 mg) was added and stirred for 1 hour. The reaction mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-chloro-3,3-dimethyl-2,4-dioxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (270 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe collected organic layer was washed sequentially with water and saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionAfter the resulting residue was dissolved in dichloromethane (14 ml)
  6. additionmanganese dioxide (684 mg) was added
  7. stirringstirred for 50 minutes
  8. additionfurther manganese dioxide (690 mg) was added
  9. stirringstirred for 1 hour
  10. filtrationThe reaction mixture was filtered through Celite
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d4a0ff9cb1d24e4fa99cf9be234bb249
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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