Pyridine → 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oxime

HRID 731703Notes

Reaction equation

HRID 731703 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]([C:18](=[N:22][OH:23])[CH:19]([CH3:21])[CH3:20])=[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)=[CH:5][CH:4]=1.C[Si]([N:28]=[C:29]=[O:30])(C)C.N1C=CC=CC=1>C1COCC1>[C:29]([O:23][N:22]=[C:18]([C:17]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:10][N:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=12)[CH:19]([CH3:20])[CH3:21])(=[O:30])[NH2:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 70696Trimethylsilyl isocyanateHCID 578374551-(2-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime

Product 1

HCID 578374371-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oximeYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 775 mg (2.5 mmol) of 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime in 5 ml of anhydrous THF was added 2 ml of trimethylsilyl isocyanate (85%) dropwise at 0° C. over 30 minutes. The mixture was stirred at room temperature over 48 hours, followed by addition of 500 μl pyridine. After stirring for another 4 hours the solvent was removed, and the residue was extracted with ethyl acetate three times. The combined organic layers were washed with 10% citric acid twice and dried over MgSO4. After evaporation of the solvent, 900 mg of crude product was obtained, which was purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant to yield 263 mg (29.8%) of 1-(2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oxime. Compound 1023.

Workup

  1. stirringAfter stirring for another 4 hours the solvent
  2. customwas removed
  3. extractionthe residue was extracted with ethyl acetate three times
  4. washThe combined organic layers were washed with 10% citric acid twice
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent
  7. custom900 mg of crude product was obtained
  8. customwhich was purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-06705590131645a1a909c4009f617f6f
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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