4'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acid → 4'-Trifluoromehtyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amide

HRID 1267123Notes

Reaction equation

HRID 1267123 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2].[F:23][C:24]([F:41])([F:40])[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:32]([C:37](O)=[O:38])=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:27][CH:26]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:1]([C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:37]([C:32]3[C:31]([C:28]4[CH:29]=[CH:30][C:25]([C:24]([F:23])([F:40])[F:41])=[CH:26][CH:27]=4)=[CH:36][CH:35]=[CH:34][CH:33]=3)=[O:38])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)#[N:2]

Participants

7

Reactant 4

HCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11185447HCID 11185447, compound

Product 1

HCID 98073154'-Trifluoromehtyl-biphenyl-2-carboxylic acid [4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenyl]-amideYield 90.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-[4-(3-cyano-benzyl)-piperazin-1-yl]-phenylamine (0.29 g), 4′-trifluoromethyl-biphenyl-2-carboxylic acid (0.26 g), HOBt (0.16 g), and Et3N (0.12 g) in CH2Cl2 (15 mL) was added at room temperature EDCl (0.23 g) and the mixture was stirred at room temperature for 4 hours. The organic solution was then washed with water, with a saturated solution of NaHCO3 and dried over Na2SO4. After filtration and evaporation of the filtrate, the residue was purified by flash chromatography eluting with CH2Cl2/AcOEt (90/10) and the solid obtained was recrystallized from EtOH to give the title compound (0.48 g) as white crystals.

Workup

  1. washThe organic solution was then washed with water, with a saturated solution of NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation of the filtrate
  4. customthe residue was purified by flash chromatography
  5. washeluting with CH2Cl2/AcOEt (90/10)
  6. customthe solid obtained
  7. customwas recrystallized from EtOH

Sources & evidence

ORD record
ord-7e2b3068d1ed4ab4bbaf7da4cd15c816
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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