Potassium Carbonate → HCID 69185505, compound

HRID 2373233Notes

Reaction equation

HRID 2373233 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH:26]=[O:27])=[C:10]([CH2:19][CH2:20][C:21]([O:23]CC)=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].[N+:28]([CH:30](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:31])#[C-:29].C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([C:26]3[O:27][CH:29]=[N:28][C:30]=3[CH3:31])=[C:10]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzeneHCID 86602412HCID 86602412, compound

Product 1

HCID 69185505HCID 69185505, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl 3-[1-ethyl-6-formyl-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoate (30 mg), 1-[(1-isocyanoethyl)sulfonyl]-4-methylbenzene (17.6 mg), potassium carbonate (17 mg) in MeOH (1 ml) was refluxed for 1.5 hours. After cooling, the mixture was diluted with water and extracted with EtOAc. The aqueous layer was acidified to pH3-4 by adding 1N HCl and extracted with CHCl3. The organic layer was washed with water, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by preparative thin layer chromatography eluting with a mixture of MeOH and CHCl3 (1:10). Crystallization from EtOAc-n-hexane gave 3-[1-ethyl-6-(4-methyl-1,3-oxazol-5-yl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]propanoic acid (10 mg) as a colorless crystal.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. additionby adding 1N HCl
  5. extractionextracted with CHCl3
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by preparative thin layer chromatography
  10. washeluting with a mixture of MeOH and CHCl3 (1:10)
  11. customCrystallization from EtOAc-n-hexane

Sources & evidence

ORD record
ord-bdb9e74f7c0247d9b9e0cb36ab06cb2a
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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