Water → HCID 68294990, compound

HRID 1909239Notes

Reaction equation

HRID 1909239 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:24]=[N:23][N:22]([CH:25]([CH3:27])[CH3:26])[C:16]=2[N:17]=[C:18]([CH:20]=[CH2:21])[CH:19]=1)=[O:13].C[N+]1([O-])CCOCC1.[OH2:36].C[OH:38].C(Cl)Cl>C(Cl)Cl.O=[Os](=O)(=O)=O>[OH:36][CH:20]([C:18]1[CH:19]=[C:14]([C:12]([NH:11][CH2:10][C:3]2[C:4](=[O:9])[NH:5][C:6]([CH3:8])=[CH:7][C:2]=2[CH3:1])=[O:13])[C:15]2[CH:24]=[N:23][N:22]([CH:25]([CH3:27])[CH3:26])[C:16]=2[N:17]=1)[CH2:21][OH:38]

Participants

7

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 21226129Dichloromethane methanolHCID 68294850HCID 68294850, compound

Product 1

HCID 68294990HCID 68294990, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.8 g, 2.19 mmol) in DCM (10 mL), N-Methylmorpholine-N-oxide (0.769 g, 6.57 mmol) was added at 0° C. Then OsO4 (2.5% in t-BuOH) (0.139 g, 5.56 mL, 0.547 mmol) was added to it. Resulting solution was stirred at room temperature for 1 h. After completion of reaction, water was added to it and extraction was carried out using 20% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give the desired product (0.66 g, 75.4%).

Workup

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude material which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9617cd32a3ee497f87db744bbc635a19
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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