5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide → 2-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(E)-2-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazole

HRID 2235718Notes

Reaction equation

HRID 2235718 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[CH:14]=[CH:15]/[C:16]([NH:18][NH:19][C:20](=O)[CH:21]([C:26]2[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=2)[CH2:22][CH2:23][CH2:24][Cl:25])=[O:17])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]1>P(Cl)(Cl)(Cl)=O>[Cl:25][CH2:24][CH2:23][CH2:22][CH:21]([C:20]1[O:17][C:16](/[CH:15]=[CH:14]/[C:4]2[CH:5]=[CH:6][C:7]([N:8]3[CH:12]=[C:11]([CH3:13])[N:10]=[CH:9]3)=[C:2]([F:1])[CH:3]=2)=[N:18][N:19]=1)[C:26]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[C:28]([F:34])[CH:27]=1

Participants

3

Reactant 1

HCID 670673925-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(E)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

Product 1

HCID 670672992-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(E)-2-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazoleYield 99.6%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N′-{(E)-3-[3-fluoro-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (103 mg) in phosphorus oxychloride (2 mL) was stirred at 120° C. for 3.5 hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure to obtain 99 mg of the title compound. The property value of the compound is as follows.

Workup

  1. waitThe reaction solution was left
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ecf8b850afc45c38c167e48b576ee29
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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