Dimethylformamide → (E)-N-[1-(4-fluorophenyl)-1-methyl ethyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamide

HRID 2247519Notes

Reaction equation

HRID 2247519 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:9]=[C:10](/[CH:20]=[CH:21]/[C:22]([OH:24])=O)[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([NH2:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=1.C1C=CC2N(O)N=NC=2C=1>C(OCC)(=O)C.O.C(Cl)CCl>[F:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([NH:35][C:22](=[O:24])/[CH:21]=[CH:20]/[C:10]2[CH:11]=[CH:12][C:13]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[C:8]([O:7][CH3:6])[CH:9]=2)([CH3:33])[CH3:34])=[CH:30][CH:31]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 130256651-(4-Fluorophenyl)-1-methylethylamineHCID 59528030(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid

Product 1

HCID 59170853(E)-N-[1-(4-fluorophenyl)-1-methyl ethyl]-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylamideYield 65.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF (5 mL) solution of (E)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)acrylic acid (60 mg) obtained in Example 121, 1-(4-fluorophenyl)-1-methylethylamine (CAS#17797-10-3) (43 mg), EDC (53 mg) and HOBT (38 mg) were added at room temperature under nitrogen atmosphere, and the reaction solution was agitated at room temperature for 12 hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. The organic layer was washed with a saturated sodium chloride solution, and the organic layer was concentrated under reduced pressure after dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel chromatography (elution solvent: methanol-ethyl acetate system), and the title compound (60 mg) was obtained.

Workup

  1. customthe organic layer was partitioned
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. dry with materialafter dried over anhydrous magnesium sulfate
  5. customThe obtained residue was purified by silica gel chromatography (elution solvent: methanol-ethyl acetate system)

Sources & evidence

ORD record
ord-6b4781b31802478f9fc2e91421dda00a
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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