Water → HCID 59170803, compound

HRID 1446486Notes

Reaction equation

HRID 1446486 reaction equation
[CH2:1]1COCC1.[CH2:6]([CH:13]([NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)=[C:23]([O:33][CH3:34])[CH:22]=1)[C:14](=[O:16])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[Mg]Cl.O>C(OCC)(=O)C>[CH2:6]([CH:13]([NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]2)=[C:23]([O:33][CH3:34])[CH:22]=1)[C:14]([OH:16])([CH3:1])[CH3:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 59170797HCID 59170797, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 59170803HCID 59170803, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (1.0 mL) solution of (E)-N-(1-benzyl-2-oxopropyl)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide (12.0 mg), methyl magnesium chloride (3 MTHF solution, 198 μL) was added at −78° C., the reaction solution was allowed to be warmed to room temperature and agitated for further 1 hour. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate ethanol=10:1), and 6.8 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate ethanol=10:1)

Sources & evidence

ORD record
ord-876a5795f4f44cfea55c34be57659f9b
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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