Acetonitrile → [5-(1H-Pyrazol-4-yl)-thiophen-3-yl]-(2-pyridin-2-yl-pyrrolidin-1-yl)-methanone

HRID 2068658노트

반응식

HRID 2068658 반응식
[NH:1]1[CH:5]=[C:4]([C:6]2[S:10][CH:9]=[C:8]([C:11]([OH:13])=O)[CH:7]=2)[CH:3]=[N:2]1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(#N)C>S(Cl)(Cl)=O>[NH:2]1[CH:3]=[C:4]([C:6]2[S:10][CH:9]=[C:8]([C:11]([N:14]3[CH2:18][CH2:17][CH2:16][CH:15]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=[O:13])[CH:7]=2)[CH:5]=[N:1]1

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 27716592-(Pyrrolidin-2-yl)pyridineHCID 581101935-(1H-Pyrazol-4-YL)thiophene-3-carboxylic acid

생성물 1

HCID 44226683[5-(1H-Pyrazol-4-yl)-thiophen-3-yl]-(2-pyridin-2-yl-pyrrolidin-1-yl)-methanone수율 19.8%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

반응 조건

온도
60 °C

실험 절차

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid (0.075 g, 0.39 mmol) was suspended in thionyl chloride (1 mL) and the mixture heated at 60° C. for 1 hour. The mixture was cooled and concentrated by evaporation, azeotroping with toluene (×3). 2-Pyrrolidin-2-yl-pyridine (0.173 g, 1.17 mmol) and acetonitrile (1.5 mL) were added and the reaction mixture stirred for 30 minutes and then the solvent was removed by evaporation. The crude material was purified by HPLC, eluting with 5%-95% acetonitrile in water (0.1% formic acid) over 20 minutes. The fractions containing the desired product were evaporated, azeotroping with methanol (×3), to give the title compound as a foam (0.025 g). LCMS m/z 325.18 [M+H]+ R.T.=5.07 min (Analytical Method 2).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated by evaporation
  3. customazeotroping with toluene (×3)
  4. customthe solvent was removed by evaporation
  5. customThe crude material was purified by HPLC
  6. washeluting with 5%-95% acetonitrile in water (0.1% formic acid) over 20 minutes
  7. additionThe fractions containing the desired product
  8. customwere evaporated
  9. customazeotroping with methanol (×3)

출처 및 근거

ORD 기록
ord-9c176ed8043e44babcc0c5a61c7d426f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299063B2

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