Trimethylsilyl isocyanate → 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oxime

HRID 731696Notes

Reaction equation

HRID 731696 reaction equation
[CH:1]([C:4]1[C:12]([C:13](=[N:17][OH:18])[CH:14]([CH3:16])[CH3:15])=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].C[Si]([N:23]=[C:24]=[O:25])(C)C>C1COCC1>[C:24]([O:18][N:17]=[C:13]([C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12)[CH:14]([CH3:16])[CH3:15])(=[O:25])[NH2:23]

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 578374801-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime

Product 1

HCID 578374431-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oximeYield 45.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 376 mg (1.53 mol) of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one oxime in 2 ml of anhydrous THF was added 540 μl of trimethylsilyl isocyanate (85%) dropwise at 0° C. over 30 minutes. The reaction was stirred at room temperature overnight. Solvent was removed in vacuo, and the residue obtained was purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant to yield 200 mg (45.3%.) of 1-(2-isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one O-carbamoyl oxime. Compound 1014.

Workup

  1. customSolvent was removed in vacuo
  2. customthe residue obtained
  3. customwas purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-6951ed905ee54565879084ca6310e29c
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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