Chloride → HCID 131727446, compound

HRID 493472Notes

Reaction equation

HRID 493472 reaction equation
C(N(CC)CC)C.[C:8]1([N:14]2[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23](Cl)=[O:24])[CH:16]=[N:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][O:27][C:28]([CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][NH3+:45])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)=[O:29].[Cl-]>C(Cl)Cl>[CH3:26][O:27][C:28](=[O:29])[CH2:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][NH:45][C:23]([C:17]3[CH:16]=[N:15][N:14]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:18]=3[C:19]([F:22])([F:21])[F:20])=[O:24])=[CH:40][CH:39]=2)=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 8471TriethylamineHCID 27764451-phenyl-5-(trifluoromethyl)pyrazole-4-carbonyl chlorideHCID 131727447HCID 131727447, compound

Product 1

HCID 131727446HCID 131727446, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (275 μL, 1.97 mmol) was added under nitrogen to a mixture of 1-phenyl-5-trifluoromethyl-1H-pyrazole-4-carbonyl chloride (272 mg, 0.992 mmol) and 4′-methoxycarbonylmethoxy-biphenyl-4-ylmethyl-ammonium; chloride (304 mg, 0.986 mmol), prepared in the previous step, in 20 mL of methylene chloride at room temperature. The reaction was stirred at room temperature for 6 h. The reaction was extracted with water, 5% NaHCO3, dried (MgSO4) and the solvent removed under reduced pressure to give methyl({4′-[({[1-phenyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]carbonyl}amino)methyl][1,1′-biphenyl]-4-yl}oxy)acetate (508 mg, 100%) as a white solid, mp 174-176° C. Elemental Analysis for C27H22F3N3O4+0.07 CH2Cl2. Calc'd C, 63.08; H, 4.33; N, 8.15. Found: C, 63.01; H, 4.17; N, 8.16.

Workup

  1. extractionThe reaction was extracted with water, 5% NaHCO3
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d3471379ee8245948d7ffc03da764a51
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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