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

HRID 2235714Notes

Reaction equation

HRID 2235714 reaction equation
[F:1]/[C:2](=[CH:23]\[C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]2)=[C:26]([O:36][CH3:37])[CH:25]=1)/[C:3]([NH:5][NH:6][C:7](=O)[CH:8]([C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[CH:14]=1)[CH2:9][CH2:10][CH2:11][Cl:12])=[O:4]>P(Cl)(Cl)(Cl)=O>[Cl:12][CH2:11][CH2:10][CH2:9][CH:8]([C:7]1[O:4][C:3](/[C:2](/[F:1])=[CH:23]/[C:24]2[CH:29]=[CH:28][C:27]([N:30]3[CH:34]=[C:33]([CH3:35])[N:32]=[CH:31]3)=[C:26]([O:36][CH3:37])[CH:25]=2)=[N:5][N:6]=1)[C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[CH:14]=1

Participants

3

Reactant 1

HCID 668388825-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N'-{(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide

Product 1

HCID 668393462-[4-chloro-1-(3,4,5-trifluorophenyl)butyl]-5-{(Z)-1-fluoro-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-[1,3,4]oxadiazoleYield 99.8%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A solution of 5-chloro-2-(3,4,5-trifluorophenyl)pentanoic acid N′-{(Z)-2-fluoro-3-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]acryloyl}hydrazide (84 mg) in phosphorus oxychloride (1 mL) was stirred at 120° C. for 7.5 hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure to obtain 81 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-052a6e8f6d3c4d34b582bcc5bd3a5dd6
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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