Water → HCID 178429118, compound

HRID 384481Notes

Reaction equation

HRID 384481 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C@H:21]2[CH2:26][CH2:25][C@H:24]([NH:27][C:28]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[CH2:23][CH2:22]2)[C:10]=1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:38]I.O>C1COCC1.CN(C=O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C@H:21]2[CH2:22][CH2:23][C@H:24]([N:27]([CH3:38])[C:28]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[O:29])[CH2:25][CH2:26]2)[C:10]=1[CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 178429119HCID 178429119, compound

Product 1

HCID 178429118HCID 178429118, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a mixed solution (10 mL) of N-(trans-4-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}cyclohexyl)cyclopentanecarboxamide (260 mg) in THF-DMF (1:1) was added 60% sodium hydride (45 mg) under ice-cooling, followed by stirring at the same temperature. Methyl iodide (0.055 mL) was added thereto, followed by stirring at room temperature for 3.5 hours. The reaction mixture was ice-cooled, and 60% sodium hydride (45 mg) and methyl iodide (0.055 mL) were added thereto, followed by stirring at room temperature for another 17 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜50/50), and the solvent was evaporated under reduced pressure. The residue was dried under vacuum at room temperature to obtain 93 mg of N-(trans-4-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}cyclohexyl)-N-methylcyclopentanecarboxamide as a colorless viscous substance.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 3.5 hours
  3. temperaturecooled
  4. stirringby stirring at room temperature for another 17 hours
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0˜50/50)
  10. customthe solvent was evaporated under reduced pressure
  11. customThe residue was dried under vacuum at room temperature

Sources & evidence

ORD record
ord-1c56e0137ffe4e14ab77781f1061f9b9
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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