Water → HCID 68294990, compound

HRID 1854068Notes

Reaction equation

HRID 1854068 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-])CC[O:32]CC1.CC(O)(C)C.[OH2:41]>C(Cl)Cl.O=[Os](=O)(=O)=O.CO.C(Cl)Cl>[OH:41][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:32]

Participants

8

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 68294850HCID 68294850, compound

Product 1

HCID 68294990HCID 68294990, compoundYield 75.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

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 2.5% OsO4 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 compound (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-589ad09a5a0a422d983adbd38a7b5a1e
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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