Water → N-(4-benzoyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramide

HRID 2186774Notes

Reaction equation

HRID 2186774 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(C(C)C)C(C)C)C.[F:25][C:26]([F:44])([F:43])[C:27]1[CH:28]=[C:29]([C:37]([CH3:42])([CH3:41])[C:38](Cl)=[O:39])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1.O>ClCCl>[C:8]([C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:1][C:38](=[O:39])[C:37]([C:29]1[CH:28]=[C:27]([C:26]([F:25])([F:43])[F:44])[CH:32]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:30]=1)([CH3:42])[CH3:41])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 118200523-Amino-4-benzoylpyridine

Product 1

HCID 18185386N-(4-benzoyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-isobutyramideYield 24.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 397 mg (2 mmol) 3-amino-4-benzoylpyridine and 517 mg (4 mmol) N-ethyldiisopropylamine in 8 ml dichloromethane was cooled in an ice bath and a solution of 765 mg (2.4 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 8 ml dichloromethane was added dropwise. The reaction mixture was warmed to room temperature and was stirred overnight. Water (5 ml) was added and the organic layer was separated. The aqueous phase was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate) and evaporated. The residue was purified by flash chromatography to give 235 mg (24%) of the title compound as orange oil.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-63db7d7e1f31466b94d79c3875f5a597
Source dataset
uspto-grants-2002_06
Patent number
US06407111B1

Reaction notes

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