HCID 68295079, compound → HCID 86703441, compound

HRID 1501691Notes

Reaction equation

HRID 1501691 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]([OH:18])CO)[CH:11]=[C:10]([C:19]([NH:21][CH2:22][C:23]4[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=4[CH3:29])=[O:20])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1.O>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]=[O:18])[CH:11]=[C:10]([C:19]([NH:21][CH2:22][C:23]4[C:24](=[O:31])[NH:25][C:26]([CH3:30])=[CH:27][C:28]=4[CH3:29])=[O:20])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 68295079HCID 68295079, compound

Product 1

HCID 86703441HCID 86703441, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a stirred solution of 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, 1.4 mmol) in 50% THF/Water (16 mL), was added NaIO4 (0.9 g, 4.2 mmol) at 0° C. and stirred at room temperature for 1 h. After completion of reaction, solvent was removed under reduced pressure and water was added to it. Extraction was 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 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-formyl-1H-indazole-4-carboxamide (0.4 g, 72.1%).

Workup

  1. customAfter completion of reaction, solvent
  2. customwas removed under reduced pressure and water
  3. additionwas added to it
  4. extractionExtraction
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford crude material which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d27a6e92446f4c90a79303d96a26a4b5
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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