Methyl iodide → HCID 66961618, compound

HRID 2247625Notes

Reaction equation

HRID 2247625 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:12]2[CH2:17][CH2:16][CH2:15]/[C:14](=[CH:18]\[C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)=[C:21]([O:31][CH3:32])[CH:20]=3)/[C:13]2=[O:33])[C@H:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1.[H-].[Na+].CI.O.[C:39](=O)(O)[O-].[Na+]>C(OCC)(=O)C.C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:12]2[CH2:17][CH2:16][CH2:15]/[C:14](=[CH:18]\[C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)=[C:21]([O:31][CH3:32])[CH:20]=3)/[C:13]2=[O:33])[C@H:9]([O:11][CH3:39])[CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66960303HCID 66960303, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66961618HCID 66961618, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a THF (1 mL) solution of (E)-1-(1-(4-fluorophenyl)-(1R,2R)-2-hydroxy propyl)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)piperidin-2-one (4 mg) obtained in Example 1119, sodium hydride (40% mineral oil content, 0.5 mg) was added, and the reaction solution was agitated at room temperature for 30 minutes. Methyl iodide (2 mg) was added to the reaction solution, and the reaction solution was agitated at room temperature for 2 hours. Saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer obtained was dried over magnesium sulfate and concentrated under reduced pressure. By purifying the residue with silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: ethyl acetate->ethyl acetate:methanol 9:1), 3 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. stirringthe reaction solution was agitated at room temperature for 2 hours
  2. customthe organic layer was partitioned
  3. customThe organic layer obtained
  4. dry with materialwas dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customBy purifying the residue
  7. washwith silica gel chromatography (Carrier: Chromatorex™ NH, elution solvent: ethyl acetate->ethyl acetate:methanol 9:1)

Sources & evidence

ORD record
ord-4fd076b08fc848c29f09448f159b9e77
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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