N-Hydroxypicolinimidamide → cis-2-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acid

HRID 1070502Notes

Reaction equation

HRID 1070502 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[NH2:4].[CH:11]12[CH2:16][CH:15]1[C:14](=O)[O:13][C:12]2=[O:18]>CN(C)C=O>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:3]1[N:4]=[C:14]([C@H:15]2[CH2:16][C@H:11]2[C:12]([OH:18])=[O:13])[O:1][N:2]=1

Participants

4

Reactant 2

HCID 120564N-HydroxypicolinimidamideHCID 27347213-Oxabicyclo(3.1.0)hexane-2,4-dione

Product 1

HCID 12018241cis-2-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

N′-hydroxy-2-pyridinecarboximidamide (0.137 g) with 3-oxabicyclo[3.1.0]hexane-2,4-dione (0.112 g) in dimethylformamide (2 drops) was heated for 4 times 30 seconds in a CEM MARS 5 microwave at 100% of 300 W to leave a fused mass. The reaction was allowed to cool and triturated with diethyl ether and filtered to leave cis-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acid (0.200 g).

Workup

  1. customto leave a fused mass
  2. temperatureto cool
  3. customtriturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-eef35b8aea374f8f847d816dbaa9eb88
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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