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 1009374Notes

Reaction equation

HRID 1009374 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-9f6fe72391f94357be881b21a5c6c6d4
Source dataset
uspto-grants-2011_07
Patent number
US07973033B2

Reaction notes

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