3-Fluorobenzoic Acid → 3-fluorobenzoic acid N'-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

HRID 1009343Notes

Reaction equation

HRID 1009343 reaction equation
C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH3:13][O:14][C:15]1[CH:16]=[C:17](/[CH:27]=[CH:28]/[C:29]([NH:31][NH2:32])=[O:30])[CH:18]=[CH:19][C:20]=1[N:21]1[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]1.[F:33][C:34]1[CH:35]=[C:36]([CH:40]=[CH:41][CH:42]=1)[C:37](O)=[O:38].C(N(C(C)C)CC)(C)C>CN(C=O)C.O.C(OCC)(=O)C.C(Cl)CCl>[CH3:13][O:14][C:15]1[CH:16]=[C:17](/[CH:27]=[CH:28]/[C:29]([NH:31][NH:32][C:37](=[O:38])[C:36]2[CH:40]=[CH:41][CH:42]=[C:34]([F:33])[CH:35]=2)=[O:30])[CH:18]=[CH:19][C:20]=1[N:21]1[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]1

Participants

9

Reactant 4

HCID 99683-Fluorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66839298(E)-3-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride

Product 1

HCID 670673443-fluorobenzoic acid N'-{(E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazideYield 62.7%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

HOBT (70 mg) and EDC (100 mg) were added to a solution of (E)-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acrylic acid hydrazide dihydrochloride (120 mg), 3-fluorobenzoic acid (49 mg) and IPEA (0.37 mL) in DMF, and the reaction solution was stirred at room temperature for 12 hours. Ethyl acetate and water were added to the reaction solution, and the precipitated solid was collected by filtration to obtain 86 mg of the title compound. The property value of the compound is as follows.

Workup

  1. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-fd3c1afdc63c4a8a9012d7e5f3d4388e
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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