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

HRID 2225147ノート

反応式

HRID 2225147 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-75311ba186c54018a22aff3881ffe0ff
出典データセット
uspto-grants-2008_05
特許番号
US07378409B2

反応ノート

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