Pyridine → HCID 57837516, compound

HRID 731698Notes

Reaction equation

HRID 731698 reaction equation
[CH3:1][CH:2]([CH3:21])[C:3]([C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12)=[N:4][OH:5].C[Si]([N:26]=[C:27]=[O:28])(C)C.N1C=CC=CC=1>C1COCC1>[C:27]([O:5][N:4]=[C:3]([C:6]1[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12)[CH:2]([CH3:21])[CH3:1])(=[O:28])[NH2:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 70696Trimethylsilyl isocyanateHCID 57837517HCID 57837517, compound

Product 1

HCID 57837516HCID 57837516, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 630 mg (2.24 mmol) of 2-methyl-1-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one oxime in 2 ml of anhydrous THF was added 600 μl of trimethylsilyl isocyanate (85%) dropwise at 0° C. over 30 minutes. The mixture was stirred at room temperature overnight, followed by the addition of 500 μl pyridine and stirring for another 4 hours. The 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 482 mg (66.3%) of 2-methyl-1-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one O-carbamoyl oxime. Compound 1017.

Workup

  1. stirringstirring for another 4 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue obtained
  4. customwas purified on an aluminum oxide column with hexane-dichloromethane-ethyl acetate as eluant

Sources & evidence

ORD record
ord-89f3e525798e4945b01ae56f19137976
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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