3-Chlorothiophene-2-carbonyl chloride → 2-[5-(3-Chloro-2-thienyl)-1,2,4-oxadiazol-3-yl]pyrazine

HRID 2114932Notes

Reaction equation

HRID 2114932 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7](=[N:9][OH:10])[NH2:8].[Cl:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17](Cl)=O>>[Cl:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]1[O:10][N:9]=[C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)[N:8]=1

Participants

3

Reactant 2

HCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 2737233N'-Hydroxy-2-pyrazinecarboximidamide

Product 1

HCID 99432262-[5-(3-Chloro-2-thienyl)-1,2,4-oxadiazol-3-yl]pyrazine

Procedure

The title compound was prepared from pyrazine-2-amidoxime (42.2 mg, 0.306 mmol) and 3-chloro-thiophene-2-carbonyl chloride (55 mg, 0.30 mmol) similar to Example 16, and yielded 67.4 mg (84%) of white solid. 1H NMR (CDCl3): 9.45 (d, J=1.37 Hz, 1H), 8.81 (dd, J=2.48, 1.65 Hz, 1H), 8.77 (d, J=2.47 Hz, 1H), 7.66 (d, J=4.95 Hz, 1H), 7.16 (d, J=5.50 Hz, 1H).

Sources & evidence

ORD record
ord-ffab7f8d880548c884451bf896ea1280
Source dataset
uspto-grants-2008_10
Patent number
US07435750B2

Reaction notes

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