Water → HCID 68295079, compound

HRID 1854137Notes

Reaction equation

HRID 1854137 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]=[CH2:16])[CH:11]=[C:10]([C:17]([NH:19][CH2:20][C:21]4[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=4[CH3:27])=[O:18])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[N+]1([O-])CC[O:34]CC1.[OH2:38]>C(Cl)Cl.O=[Os](=O)(=O)=O>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]([OH:34])[CH2:16][OH:38])[CH:11]=[C:10]([C:17]([NH:19][CH2:20][C:21]4[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=4[CH3:27])=[O:18])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 68295090HCID 68295090, compound

Product 1

HCID 68295079HCID 68295079, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-vinyl-1H-indazole-4-carboxamide (0.9 g, 2.3 mmol) in DCM (10 mL), was added N-methylmorpholine-N-oxide (0.81 g, 6.92 mmol) at 0° C. OsO4 (0.147 g, 0.576 mmol, 2.5% solution in t-BuOH) was then added. The resulting solution was stirred at room temperature for 1 h. After completion of reaction, water was added and extraction carried out using 10% 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 title compound 1-cyclopentyl-6-(1,2-dihydroxyethyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide (0.6 g, 61.3%).

Workup

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

Sources & evidence

ORD record
ord-74d241ad62cc434f9b30e07a1497e27f
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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