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

HRID 42942Notes

Reaction equation

HRID 42942 reaction equation
N#N.[OH:3][CH:4]([C:6]1[O:7][C:8]([CH2:11][N:12]2[N:16]=[C:15]([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])[CH:14]=[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[N:16]=[C:15]([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])[CH:14]=[N:13]2)=[CH:9][N:10]=1)(=[O:3])[CH3:5]

Participants

5

Reactant 2

HCID 947NitrogenHCID 673662405-Phenyl-oxazole-4-carboxylic acid {2-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-2H-[1,2,3]triazol-4-yl}-amide

Product 1

HCID 426439165-Phenyl-oxazole-4-carboxylic acid [2-(2-acetyl-oxazol-5-ylmethyl)-2H-[1,2,3]triazol-4-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 {2-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-2H-[1,2,3]triazol-4-yl}-amide (60 mg, 0.16 mmol) in AcCN (1.6 mL) was treated at rt with MnO2 (114 mg, 1.18 mmol) and the reaction mixture was stirred at rt overnight before being filtered through Celite. The solvent was removed under reduced pressure and the residue was dissolved in EA (10 mL), washed with water (10 mL), and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a white foam. LC-MS-conditions 02: tR=0.97 min; [M+H]+=379.06.

Workup

  1. filtrationbefore being filtered through Celite
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in EA (10 mL)
  4. washwashed with water (10 mL), and brine
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-4d2287d3714346128aa814709186d15d
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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