Pyrrolidine → 2-(3-Ethylureido)-5-(trifluoromethyl)benzoic acid

HRID 1455334Notes

Reaction equation

HRID 1455334 reaction equation
[CH2:1]([NH:3][C:4](=[O:22])[NH:5][C:6]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:7]=1[C:8]([O:10]CC=C)=[O:9])[CH3:2].N1CCCC1>C(#N)C>[CH2:1]([NH:3][C:4](=[O:22])[NH:5][C:6]1[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:19])[F:21])=[CH:14][C:7]=1[C:8]([OH:10])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 21075131Allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate

Product 1

HCID 222687522-(3-Ethylureido)-5-(trifluoromethyl)benzoic acidYield 56.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation B1, Step 3: The allyl 2-(3-ethylureido)-5-(trifluoromethyl)benzoate (1.8 g, ca. 5.7 mmol) was dissolved in acetonitrile (50 mL) The solution was charged with pyrrolidine (1.0 mL, 12 mmol) and Ph(PPh3)4 (140 mg, 0.17 mmol) and then stirred for 2 h at RT before being concentrated in vacuo. The residue was diluted with EtOAc and this was washed successively with 1N HCl (2×) and brine (1×) before being dried (Na2SO4), filtered, and concentrated in vacuo. The residue was triturated with methylene chloride to afford pure 2-(3-ethylureido)-5-(trifluoromethyl)benzoic acid (0.89 g).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washthis was washed successively with 1N HCl (2×) and brine (1×)
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with methylene chloride

Sources & evidence

ORD record
ord-5641765c18034d9ea7053e55b6bbda64
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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