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

HRID 2225147노트

반응식

HRID 2225147 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75311ba186c54018a22aff3881ffe0ff
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378409B2

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