Imidazole → HCID 67067409, compound

HRID 1009426Notes

Reaction equation

HRID 1009426 reaction equation
N1C=CN=C1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[CH:44]=[CH:45]/[C:46]([NH:48][NH:49][C:50](=[O:62])[CH2:51][CH2:52][CH2:53][C:54](=[O:61])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=O)[CH:35]=[CH:36][C:37]=1[N:38]1[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]1>C(Cl)Cl>[CH3:30][O:31][C:32]1[CH:33]=[C:34](/[CH:44]=[CH:45]/[C:46]2[O:62][C:50]([CH2:51][CH:52]=[CH:53][C:54]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:61])=[N:49][N:48]=2)[CH:35]=[CH:36][C:37]=1[N:38]1[CH:42]=[C:41]([CH3:43])[N:40]=[CH:39]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67067313HCID 67067313, compound

Product 1

HCID 67067409HCID 67067409, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

IPEA (2.5 mL) was added to a suspension of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid hydrazide (500 mg) in methylene chloride (12 mL) at room temperature, and the reaction solution was stirred at room temperature for 10 minutes. 4-benzoylbutyric acid (334 mg) and BOPCl (442 mg) were added to the reaction solution at room temperature, and the reaction solution was stirred at room temperature for four hours. A saturated sodium bicarbonate solution was added to the reaction solution, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure to obtain 5-oxo-5-phenylpentanoic acid N′-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (692 mg). Imidazole (494 mg), carbon tetrabromide (2.36 g) and triphenylphosphine (559 mg) were added to a suspension of 5-oxo-5-phenylpentanoic acid N′-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (634 mg) in methylene chloride (15 mL) at room temperature, and the reaction solution was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system, then ethyl acetate-methanol system) to obtain 515 mg of the title compound. The property value of the compound is as follows.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (
  3. washelution solvent

Sources & evidence

ORD record
ord-5255c0c1d937494ea998e334c37dc4bb
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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