Ethyl Acetate → 2-(3,5-bis-trifluoromethyl-phenyl)-N-(2'-methoxy-biphenyl-2-yl)-N-methyl-isobutyramide

HRID 1267517Notes

Reaction equation

HRID 1267517 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][CH3:16].C(N(C(C)C)C(C)C)C.[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([C:38]([CH3:43])([CH3:42])[C:39](Cl)=[O:40])[CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1.C(OCC)(=O)C>C(Cl)Cl>[F:26][C:27]([F:45])([F:44])[C:28]1[CH:29]=[C:30]([C:38]([CH3:43])([CH3:42])[C:39]([N:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH3:16])=[O:40])[CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 112671412-(3,5-Bis(trifluoromethyl)phenyl)-2-methylpropanoyl chlorideHCID 12555621HCID 12555621, compound

Product 1

HCID 185464902-(3,5-bis-trifluoromethyl-phenyl)-N-(2'-methoxy-biphenyl-2-yl)-N-methyl-isobutyramideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 53 mg (0.25 mmol) (2′-methoxy-biphenyl-2-yl)-methyl-amine and 0.064 ml (0.375 mmol) N-ethyldiisopropylamine in 4 ml CH2Cl2 was cooled in an ice bath and a solution of 88 mg (0.275 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl chloride in 1 ml CH2Cl2 was added dropwise. The reaction mixture was stirred overnight at room temperature. Ethyl acetate was added and the organic layer was washed with saturated Na2CO3 solution, 1 N HCl solution, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2, hexane/ethyl acetate 4:1) to give 107 mg (87%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(2′-methoxy-biphenyl-2-yl)-N-methyl-isobutyramide as orange crystals, MS (ISP): 496.1 (M+H)+.

Workup

  1. washthe organic layer was washed with saturated Na2CO3 solution, 1 N HCl solution
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography (SiO2, hexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-194441f493964a07bd990730c4313085
Source dataset
uspto-grants-2003_04
Patent number
US06552088B2

Reaction notes

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