4'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acid → HCID 69871373, compound

HRID 1267119Notes

Reaction equation

HRID 1267119 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:21][C:22]([F:39])([F:38])[C:23]1[CH:28]=[CH:27][C:26]([C:29]2[C:30]([C:35](O)=[O:36])=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:24]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CCN(CC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:35]([C:30]3[C:29]([C:26]4[CH:27]=[CH:28][C:23]([C:22]([F:21])([F:38])[F:39])=[CH:24][CH:25]=4)=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:36])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 552514'-(Trifluoromethyl)(1,1'-biphenyl)-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21940085tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate

Product 1

HCID 69871373HCID 69871373, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-(4-aminophenyl)-piperidine-1-carboxylic acid tert-butyl ester (0.18 g), 4′-trifluoromethyl-biphenyl-2-carboxylic acid (0.17 g), HOBt (0.1 g), and Et3N (80 mg) in CH2Cl2 (10 mL) was added at room temperature EDCl (0.15 g) and the mixture was stirred at room temperature for 16 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 petroleum ether/AcOEt (70/30) to give the title compound (0.25 g) as an orange oil.

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 petroleum ether/AcOEt (70/30)

Sources & evidence

ORD record
ord-cd0e3f1ec52248b8b3c6f1ef95aff3ef
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Reaction notes

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