Nitrogen → 5-Phenyl-oxazole-4-carboxylic acid [1-(2-acetyl-oxazol-5-ylmethyl)-1H-pyrazol-3-yl]-amide

HRID 2065365Notes

Reaction equation

HRID 2065365 reaction equation
N#N.[OH:3][CH:4]([C:6]1[O:7][C:8]([CH2:11][N:12]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[CH:22][O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:19])=[N:13]2)=[CH:9][N:10]=1)[CH3:5]>C(C#N)(C)=O.O=[Mn]=O>[C:4]([C:6]1[O:7][C:8]([CH2:11][N:12]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]3[N:21]=[CH:22][O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:19])=[N:13]2)=[CH:9][N:10]=1)(=[O:3])[CH3:5]

Participants

5

Reactant 2

HCID 947NitrogenHCID 669293865-Phenyl-oxazole-4-carboxylic acid {1-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-1H-pyrazol-3-yl}-amide

Product 1

HCID 669291615-Phenyl-oxazole-4-carboxylic acid [1-(2-acetyl-oxazol-5-ylmethyl)-1H-pyrazol-3-yl]-amide

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-phenyl-oxazole-4-carboxylic acid {1-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-1H-pyrazol-3-yl}-amide (140 mg, 0.37 mmol) in AcCN (4.0 mL) was treated at rt with MnO2 (267 mg, 2.77 mmol) and the reaction mixture was stirred at rt overnight before being filtered through Celite. Purification of the residue by FC (3:7 hept-EA) gave the title compound as a white foam. TLC: rf (3:7 hept-EA)=0.28. LC-MS-conditions 02: tR=0.95 min; [M+H]+=378.21.

Workup

  1. filtrationbefore being filtered through Celite
  2. customPurification of the residue by FC (3:7 hept-EA)

Sources & evidence

ORD record
ord-ae5563a4825c4d4a8a816e654ef7f8ac
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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