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

HRID 577762노트

반응식

HRID 577762 반응식
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:13]=[C:12]2[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]2=[CH:10][C:9]=1[CH:19]=[O:20].[CH:21]1([CH2:25][NH:26][CH2:27][CH3:28])[CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C.C(OCC)(=O)C>[CH:21]1([CH2:25][N:26]([CH2:27][CH3:28])[C:8]2[N:13]=[C:12]3[N:14]([CH3:18])[N:15]=[C:16]([CH3:17])[C:11]3=[CH:10][C:9]=2[CH:19]=[O:20])[CH2:24][CH2:23][CH2:22]1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162286606-Chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehydeHCID 23366322(Cyclobutylmethyl)(ethyl)amine

생성물 1

HCID 574444326-(cyclobutylmethyl-ethyl-amino)-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde수율 87%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Potassium carbonate (0.83 g, 6 mmol) was added to a solution of 6-chloro-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (1.04 g, 5.0 mmol) and cyclobutylmethyl-ethyl-amine (0.8 g, 7.0 mmol) in anhydrous DMF (8 mL) under nitrogen. After stirring for 0.5 h at RT, the reaction mixture was heated for 14 h at 80° C. Thereafter, the reaction was cooled to RT, water (30 mL) and ethyl acetate (30 mL) were added, and the organic layer was separated from the aqeous mixture. The organic extract was washed with brine, dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by chromatography using silica gel (200-400 mesh) and eluted with 20-60% hexane:ethyl acetate to afford the title compound as a pale yellow liquid (1.23 g), yield: 87%.

후처리

  1. temperaturethe reaction mixture was heated for 14 h at 80° C
  2. temperatureThereafter, the reaction was cooled to RT
  3. customthe organic layer was separated from the aqeous mixture
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography
  9. washeluted with 20-60% hexane

출처 및 근거

ORD 기록
ord-e193743bd3dc4affa737307cd7b167ee
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040558B2

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