Tributylamine → HCID 68612195, compound

HRID 1848286Notes

Reaction equation

HRID 1848286 reaction equation
[C:1]([C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11]N2C=CC=CC2)=[O:9])=[C:6]([CH3:20])[CH:5]=1)(=[O:3])[CH3:2].[Cl:21][C:22]1[CH:23]=[C:24]([C:29](=[O:34])[C:30]([F:33])([F:32])[F:31])[CH:25]=[C:26]([Cl:28])[CH:27]=1.C([N:39]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:40]CCC)CCC>C1(C)C=CC=CC=1>[Cl:21][C:22]1[CH:23]=[C:24]([C:29]([OH:34])([C:30]([F:31])([F:32])[F:33])[CH2:2][C:1]([C:4]2[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH2:11][C:44]3[CH:45]=[CH:46][CH:47]=[CH:40][N:39]=3)=[O:9])=[C:6]([CH3:20])[CH:5]=2)=[O:3])[CH:25]=[C:26]([Cl:28])[CH:27]=1

Participants

5

Reactant 3

HCID 7622TributylamineHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 68613334HCID 68613334, compound

Product 1

HCID 68612195HCID 68612195, compoundYield 150.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

1.52 g of 4-acetyl-2-methyl-N-(pyridin-1-ylmethyl)benzoic acid amide, 1.51 g of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 1.51 g of toluene and 0.52 g of tri-n-butylamine were fed and the mixture was stirred for 10 hours at 60° C. The mixture was left to cool to room temperature and 1 ml of toluene was added to the slurry-state reaction solution. The slurry was filtered under reduced pressure, and the solid was washed with a small amount of toluene. 2.16 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-methyl-N-(pyridin-2-ylmethyl)benzoic acid amide as a flesh color solid was obtained by drying under reduced pressure.

Workup

  1. waitThe mixture was left
  2. temperatureto cool to room temperature
  3. filtrationThe slurry was filtered under reduced pressure
  4. washthe solid was washed with a small amount of toluene

Sources & evidence

ORD record
ord-3baefc41134c409cbd789b42bab0a863
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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