Sodium Hydroxide → 6-bromo-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1501531노트

반응식

HRID 1501531 반응식
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:18]([O:20]CC)=O)[C:7]2[CH:12]=[N:11][N:10]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:8]=2[N:9]=1.[NH2:23][CH2:24][C:25]1[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=1[CH3:31].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CCO.CS(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([C:18]([NH:23][CH2:24][C:25]2[C:26](=[O:33])[NH:27][C:28]([CH3:32])=[CH:29][C:30]=2[CH3:31])=[O:20])[C:7]2[CH:12]=[N:11][N:10]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17]3)[C:8]=2[N:9]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 86703404HCID 86703404, 화합물

생성물 1

HCID 867034146-bromo-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide수율 70%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 702Ethanol용매2회

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온도
60 °C

실험 절차

Aqueous NaOH (0.308 g, 7.72 mmol) was added to a solution of ethyl 6-bromo-1-cyclopentyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (1.3 g, 3.8 mmol) in EtOH (10 mL) and stirred at 60° C. for 1 h. After completion of the reaction, ethanol was removed under reduced pressure and it was acidified using 10% citric acid solution. Extraction was carried out using ethyl acetate; the combined organic layers were washed with water, brine and dried over anhydrous Na2SO4; filtered and concentrated under reduced pressure. The crude acid (1 g, 3.23 mmol) was then dissolved in DMSO (10 mL) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.98 g, 6.47 mmol) was added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (2.52 g, 4.85 mmol) was added to it and stirring was continued overnight. After completion of the reaction, reaction mass was poured into ice to obtain solid, which was filtered and washed with acetonitrile followed by ether to provide the desired intermediate (1 g, 70%).

후처리

  1. customwas removed under reduced pressure and it
  2. extractionExtraction
  3. washthe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionwas added to it
  8. stirringstirring
  9. waitwas continued overnight
  10. customAfter completion of the reaction, reaction mass
  11. additionwas poured into ice
  12. customto obtain solid, which
  13. filtrationwas filtered
  14. washwashed with acetonitrile

출처 및 근거

ORD 기록
ord-7804817ed6574b3aace6b3310a90d20f
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206157B2

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