Water → 3-(5-Chloro-pyridin-2-yl)-5-(3-methyl-3H-imidazol-4-yl)-[1,2,4]-oxadiazole

HRID 2250464Notes

Reaction equation

HRID 2250464 reaction equation
[CH3:1][N:2]1[C:6]([C:7](Cl)=[O:8])=[CH:5][N:4]=[CH:3]1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([NH:19]O)=[NH:18])=[N:15][CH:16]=1.O>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[N:19]=[C:7]([C:6]3[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=3)[O:8][N:18]=2)=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 27765541-methyl-1H-Imidazole-5-carbonyl chlorideHCID 178513304HCID 178513304, compound

Product 1

HCID 162224033-(5-Chloro-pyridin-2-yl)-5-(3-methyl-3H-imidazol-4-yl)-[1,2,4]-oxadiazoleYield 5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-methyl-3H-imidazole-4-carbonyl chloride (91 mg, 0.5 mmol), 5-chloro-N-hydroxy-pyridine-2-carboxamidine (85.8 mg, 0.5 mmol) in pyridine (5 ml) was refluxed for 4 h and then cooled to room temperature. To the solution was added water (20 ml) and the product precipitated from the solution. The solid was collected by filtration and washed with water, dried to give 6 mg (5%) of the title compound. 1H NMR (CDCl3): 8.78 (d, J=2.4 Hz, 1H), 8.15 (d, J=8.4 Hz, 1H), 8.05 (s, 1H), 7.87 (dd, J=2.7 Hz, J=8.7 Hz, 1H), 7.70 (s, 1H), 4.14 (s, 3H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customthe product precipitated from the solution
  3. filtrationThe solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b4cb6913865b49ddbcc25ff08cc416b6
Source dataset
uspto-grants-2008_01
Patent number
US07317029B2

Reaction notes

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