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

HRID 2225147Notes

Reaction equation

HRID 2225147 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). 1H-NMR (300 MHz, d4-MeOH): δ 8.59 (d, 1 H, J=9.6 Hz), 8.26 (d, 1 H, J=1.5 Hz), 7.72 (dd, 1 H, J=9.2, 1.8 Hz), 3.23 (q, 2 H, J=7.3 Hz), 1.17 (t, 3 H, J=7.2 Hz).

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-75311ba186c54018a22aff3881ffe0ff
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…