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

HRID 577766노트

반응식

HRID 577766 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-535836a3781a447b9c51e84b536077d9
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040558B2

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