Tetrahydrofuran → HCID 59170702, compound

HRID 1446541Notes

Reaction equation

HRID 1446541 reaction equation
[CH2:1]1COCC1.[CH:6]([C:8]1[CH:9]=[C:10](/[CH:19]=[CH:20]/[C:21]([NH:23][CH:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)=[O:22])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[O:7].C[Mg]Br.O.[Cl-].[NH4+]>C(OCC)(=O)C>[OH:7][CH:6]([C:8]1[CH:9]=[C:10](/[CH:19]=[CH:20]/[C:21]([NH:23][CH:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26][CH2:25]2)=[O:22])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)[CH3:1]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 57429219Ammonium chloride monohydrateHCID 59170865HCID 59170865, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59170702HCID 59170702, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (0.5 mL) solution of (E)-3-(3-formyl-4-(1H-imidazol-1-yl)phenyl)-N-indan-1-ylacrylamide (23 mg) obtained in Example 437, methyl magnesium bromide (3M ether solution, 0.04 mL) was added under nitrogen atmosphere under ice-cooling and the reaction mixture was agitated for 1 hour. A saturated ammonium chloride water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent:methanol-ethyl acetate system), and 10 mg of the title compound was obtained.

Workup

  1. temperaturecooling
  2. customthe organic layer was partitioned
  3. washThe organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (Carrier: Chromatorex™ NH, elution solvent:methanol-ethyl acetate system)

Sources & evidence

ORD record
ord-f6e12ca30d9d4ccf9c87f8c19977eaff
Source dataset
uspto-grants-2010_02
Patent number
US07667041B2

Reaction notes

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