HCID 68294990, compound → N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-formyl-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1909240Notes

Reaction equation

HRID 1909240 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]([C:17]([NH:19][CH2:20][C:21]2[C:22](=[O:29])[NH:23][C:24]([CH3:28])=[CH:25][C:26]=2[CH3:27])=[O:18])[C:8]2[CH:13]=[N:12][N:11]([CH:14]([CH3:16])[CH3:15])[C:9]=2[N:10]=1)CO>C1COCC1.O>[CH3:27][C:26]1[CH:25]=[C:24]([CH3:28])[NH:23][C:22](=[O:29])[C:21]=1[CH2:20][NH:19][C:17]([C:7]1[C:8]2[CH:13]=[N:12][N:11]([CH:14]([CH3:16])[CH3:15])[C:9]=2[N:10]=[C:5]([CH:2]=[O:1])[CH:6]=1)=[O:18]

Participants

3

Reactant 1

HCID 68294990HCID 68294990, compound

Product 1

HCID 86703427N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-formyl-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamideYield 85%

Reagents, catalysts & solvents 1

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

Procedure

To a stirred solution of 6-(1,2-dihydroxyethyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.66 g, 1.65 mmol) in 50% THF/Water (12 mL), NaIO4 (1.06 g, 4.95 mmol) was added at 0° C. and stirred at room temperature for 1 h. After completion of reaction, solid was filtered and washed with water. Azeotrope it with toluene to obtain N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-formyl-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.515 g, 84.8%).

Workup

  1. customAfter completion of reaction, solid
  2. filtrationwas filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-c21a0885cb4d4b30a4352e860d9aed8e
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

Loading…