Triethylamine → HCID 54344728, compound

HRID 1267135Notes

Reaction equation

HRID 1267135 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CCN(CC)CC.[C:39]([C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44](Cl)=[O:45])#[N:40]>C(Cl)Cl>[C:39]([C:41]1[CH:42]=[C:43]([CH:47]=[CH:48][CH:49]=1)[C:44]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]3[C:17]([C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][CH:23]=4)=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:15])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1)=[O:45])#[N:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 112010994'-Trifluoromethyl-biphenyl-2-carboxylic acid [4-(piperazinyl)-phenyl]-amide

Product 1

HCID 54344728HCID 54344728, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4′-trifluoromethyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide (0.318 g) in CH2Cl2 (15 mL) containing Et3N (79 mg) was added dropwise 3-cyano-benzoyl chloride (0.129 g) and the mixture was stirred at room temperature for 1 hour. The solution was then washed with water, with brine, dried over Na2SO4, filtered and evaporated. The residue was then purified by flash chromatography eluting with CH2Cl2/AcOEt (80/20) and the solid obtained was recrystallized from AcOEt to give the title compound (0.29 g) as white crystals.

Workup

  1. washThe solution was then washed with water, with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was then purified by flash chromatography
  6. washeluting with CH2Cl2/AcOEt (80/20)
  7. customthe solid obtained
  8. customwas recrystallized from AcOEt

Sources & evidence

ORD record
ord-a9ddeef5fb734672873513a8b017459e
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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