Water → 6-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

HRID 577766ノート

反応式

HRID 577766 の反応式
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]2=[CH:4][C:3]=1[CH:13]=[O:14].C(=O)([O-])[O-].[K+].[K+].[CH:21]1([CH2:26][NH:27][CH2:28][CH3:29])[CH2:25][CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C>[CH:21]1([CH2:26][N:27]([CH2:28][CH3:29])[C:2]2[N:7]=[C:6]3[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:5]3=[CH:4][C:3]=2[CH:13]=[O:14])[CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 43163716N-(cyclopentylmethyl)-N-ethylamine

生成物 1

HCID 574868046-(cyclopentylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A suspension of 6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (5 g, 0.023 mol) and potassium carbonate (9.9 g, 0.0717 mol) in DMF (75 mL) was stirred for 20 min at RT. Cyclopentylmethyl ethyl amine (4.25 g, 33.0 mmol) was then added and the reaction was refluxed for 8 h. After cooling the reaction to RT, water (500 mL) was added to the reaction mixture and extracted with ethyl acetate (3×400 mL) and the combined organic layers were dried and concentrated. The residue was purified by silica gel (100-200 mesh) column chromatography. Elution with 10% ethyl acetate in hexanes gave the pure product as a colorless, gummy mass (76%).

後処理

  1. temperaturethe reaction was refluxed for 8 h
  2. temperatureAfter cooling
  3. customthe reaction to RT
  4. extractionextracted with ethyl acetate (3×400 mL)
  5. customthe combined organic layers were dried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel (100-200 mesh) column chromatography
  8. washElution with 10% ethyl acetate in hexanes
  9. customgave the pure product as a colorless, gummy mass (76%)

出典と根拠

ORDレコード
ord-535836a3781a447b9c51e84b536077d9
出典データセット
uspto-grants-2015_05
特許番号
US09040558B2

反応ノート

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