2-Methyl-2H-pyrazol-3-ylamine → 1-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1924235ノート

反応式

HRID 1924235 の反応式
Cl[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:16][N:17]1[C:21]([NH2:22])=[CH:20][CH:19]=[N:18]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[NH2:22][C:21]1[N:17]([CH3:16])[N:18]=[CH:19][C:20]=1[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11]

参加物

7

反応物 4

HCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) Chloride2 回HCID 536292161-(Chloromethyl)-4-propylpyrrolidin-2-one

生成物 1

HCID 577430221-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-4-propylpyrrolidin-2-one収率 16%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
65 °C

実験手順

In a 25 ml, three-necked flask fitted with a magnetic stirrer, under inert atmosphere, 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 (0.136 g, 0.77 mmol) is added dropwise to a suspension of AlCl3 (0.033 g, 0.25 mmol) in TCE at 0° C. In another 25 ml, three-necked flask fitted with a magnetic stirrer and reflux condenser under inert atmosphere, 1-methyl-1H-pyrazol-5-amine x64 (0.05 g, 0.51 mmol) is dissolved in TCE (10 ml) and the mixture is heated at 65° C. At this temperature, the solution containing compound x63 and AlCl3 is added dropwise and the mixture is heated at 80° C. for 16 h. Water and CH2Cl2 are added, the pH is brought up to 8 with sodium bicarbonate and the aqueous phase is extracted with CH2Cl2. The combined organic phases are washed with brine, dried over MgSO4, filtered and concentrated. The crude product is purified by preparative chromatography on silicagel, then by preparative chromatography on reverse phase to afford 19 mg of 1-[(5-amino-1-methyl-1H-pyrazol-4-yl)methyl]-4-propylpyrrolidin-2-one 170.

後処理

  1. customIn another 25 ml, three-necked flask fitted with a magnetic stirrer
  2. dissolutionis dissolved in TCE (10 ml)
  3. additionis added dropwise
  4. temperaturethe mixture is heated at 80° C. for 16 h
  5. extractionthe aqueous phase is extracted with CH2Cl2
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product is purified by preparative chromatography on silicagel

出典と根拠

ORDレコード
ord-50cb63b4b03a4ae18c10539c478a818b
出典データセット
uspto-grants-2012_05
特許番号
US08178533B2

反応ノート

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