Picolinic acid → HCID 68630392, compound

HRID 431919Notes

Reaction equation

HRID 431919 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C([N:12]([CH2:15]C)CC)C.C(OC(Cl)=O)C(C)C.C[N:26](C)C=O>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:9][N:12]=[CH:15][N:26]=1

Participants

6

Reactant 4

HCID 1018Picolinic acidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 62365Isobutyl chloroformate

Product 1

HCID 68630392HCID 68630392, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of picolinic acid (62 mg, 0.5 mmol) and triethylamine (202 mg, 2 mmol) in tetrahydrofuran (1 mL) was treated with isobutylchloroformate (0.059 ml, 0.55 mmol) at room temperature. The mixture was stirred for 2 hours and treated with 3-fluoro-5-(1H-imidazol-1-yl)]phenyl-amidoxime (100 mg, 0.45 mmol). The mixture was then heated in dimethylformamide (1 mL) at 130° C. overnight. Standard work up, afforded 24.4 mg (17.6%) 3-[3-fluoro-5-(1H-imidazol-1-yl)]phenyl]-5-(2-pyridyl)-1,2,4-oxadiazole. 1H-NMR (CDCl3), δ (ppm): 8.90 (d, 1H), 8.32 (d, 1H), 8.10 (s, 1H), 7.7.98 (m, 3H), 7.58 (dd, 1H), 7.39 (s, 1H), 7.29 (m, 2H).

Sources & evidence

ORD record
ord-565635ba498e43ff873a58177674cd35
Source dataset
uspto-grants-2003_12
Patent number
US06660753B2

Reaction notes

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