Tetrahydrofuran → HCID 66960888, compound

HRID 2247498Notes

Reaction equation

HRID 2247498 reaction equation
C1COCC1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][C:22]([N:24]2[CH2:28][CH:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26](/[CH:35]=[N:36]/O)[CH2:25]2)=[O:23])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1.C1N=CN(C(N2C=NC=C2)=O)C=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10](/[CH:20]=[CH:21]/[C:22]([N:24]2[CH2:28][CH:27]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:26]([C:35]#[N:36])[CH2:25]2)=[O:23])[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 140496661HCID 140496661, compound

Product 1

HCID 66960888HCID 66960888, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a THF (3 ml) solution of (E)-1-{3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}-4-phenylpyrrolidine-3-carbaldehyde oxime (17.8 mg) obtained in Example 359, CDI (32.4 mg) was added at room temperature, and heat-refluxing was carried out for 3 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and saturated sodium bicarbonate solution were added to the reaction solution, and the organic layer was partitioned. After drying the obtained organic layer with anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate methanol 10:1), and the 14.6 mg (86%) title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. temperatureheat-refluxing
  2. customthe organic layer was partitioned
  3. dry with materialAfter drying the obtained organic layer with anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (elution solvent: ethyl acetate methanol 10:1)

Sources & evidence

ORD record
ord-8e0d8f6911e5421dae27602ab2d8febc
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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