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

HRID 2068658ノート

反応式

HRID 2068658 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9c176ed8043e44babcc0c5a61c7d426f
出典データセット
uspto-grants-2012_10
特許番号
US08299063B2

反応ノート

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