Methyl iodide → HCID 68006317, compound

HRID 1026601Notes

Reaction equation

HRID 1026601 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:25])[N:9]2[CH:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[N:4][CH:3]=1.[H-].[Na+].[C:28](=O)([O:32]CC)[O:29][CH2:30][CH3:31].[CH3:36]I>O.O1CCCC1>[C:21]([O:20][C:18]([N:15]1[CH2:16][CH2:17][CH:12]([N:9]2[C:10]3[C:5](=[N:4][CH:3]=[C:2]([Cl:1])[CH:11]=3)[CH2:6][C:7]([CH3:36])([C:28]([O:29][CH2:30][CH3:31])=[O:32])[C:8]2=[O:25])[CH2:13][CH2:14]1)=[O:19])([CH3:22])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 68006101HCID 68006101, compound

Product 1

HCID 68006317HCID 68006317, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a tetrahydrofuran solution (10 ml) of tert-butyl 4-(7-chloro-2-oxo-3,4-dihydro-1,5-naphthyridin-1(2H)-yl)piperidine-1-carboxylate (Reference Example 9-3) (500 mg) were added at 0° C. sodium hydride (161 mg) and diethyl carbonate (0.66 ml). After the reaction solution was stirred at 70° C. for 4 hours, methyl iodide (0.171 ml) was added at 0° C., and stirred at room temperature for 6 hours. Water was added to the reaction solution at 0° C., and extracted with ethyl acetate. The collected organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford ethyl 1-[1-(tert-butoxycarbonyl)piperidin-4-yl]-7-chloro-3-methyl-2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-carboxylate (286 mg).

Workup

  1. stirringstirred at room temperature for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe collected organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ab51403f85043b695cb61c7829a27f5
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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