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

HRID 42974
Notes
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Reaction equation

HRID 42974 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]([CH3:36])[O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:35])([F:34])[F:33])[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]([CH3:36])[O:23][C:24]=3[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:34])([F:35])[F:33])[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 673650542-Methyl-5-(3-trifluoromethoxy-phenyl)-oxazole-4-carboxylic acid {2-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl]-2H-[1,2,3]triazol-4-yl}-amide

Product 1

HCID 673652652-Methyl-5-(3-trifluoromethoxy-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 dioxideCatalyst
HCID 69430
2-Oxopropiononitrile
Solvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-methyl-5-(3-trifluoromethoxy-phenyl)-oxazole-4-carboxylic acid {2-[2-(1-hydroxy-ethyl)-oxazol-5-ylmethyl}-2H-[1,2,3]triazol-4-yl]-amide (54 mg, 0.11 mmol) in AcCN (1.5 mL) was treated at rt with MnO2 (85 mg, 0.85 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=1.09 min; [M+H]+=476.95.

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-3cc3e3f5229e4e038ed82bffc1339204
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