Trifluoroacetic acid → 4'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amide

HRID 1267116Notes

Reaction equation

HRID 1267116 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]3[C:24]([C:30]4[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=4)=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[O:22])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[N:11]1([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([C:23]3[C:24]([C:30]4[CH:31]=[CH:32][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:34][CH:35]=4)=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[O:22])=[CH:18][CH:19]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 540547824-{4-[(4'-Isopropyl-5-methyl-biphenyl-2-carbonyl)-amino]-phenyl}piperazine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 537730414'-Isopropyl-5-methyl-biphenyl-2-carboxylic acid (4-piperazin-1-yl-phenyl)-amideYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[(4′-isopropyl-5-methyl-biphenyl-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (4 g) in CH2Cl2 (20 mL) was added trifluoroacetic acid (15 mL) and the solution was stirred at room temperature for 16 hours. The mixture was then evaporated under reduced pressure and the residue was taken in water and basified with a 1N NaOH aqueous solution. The resulting precipitate was extracted with CH2Cl2 and the organic phase was washed with water, dried over Na2SO4 filtered and evaporated to give the title compound (3 g) as white crystals.

Workup

  1. customThe mixture was then evaporated under reduced pressure
  2. extractionThe resulting precipitate was extracted with CH2Cl2
  3. washthe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-490d6c6cf0684d928abb461dbcef81d2
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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