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

HRID 42972
Notes
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Reaction equation

HRID 42972 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]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[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]=[C:22]([CH3:32])[O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=3)=[O:19])[CH:14]=[N:13]2)=[CH:9][N:10]=1)(=[O:3])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 947NitrogenHCID 67365317HCID 67365317, compound

Product 1

HCID 673653075-(3-Chloro-phenyl)-2-methyl-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-(3-chloro-phenyl)-2-methyl-oxazole-4-carboxylic acid {2-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-2H-[1,2,3]triazol-4-yl}-amide (54 mg, 0.13 mmol) in AcCN (1.5 mL) was treated at rt with MnO2 (91 mg, 0.94 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 solid. LC-MS-conditions 02: tR=1.06 min; [M+H]+=426.75.

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-deb724532a474710ad16c773494cc290
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536209B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes