Water → N-(3-cyano-5-fluoro-2-pyrazinyl)benzamide

HRID 392364Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C:17]#[N:18])[C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[F-:19].[K+].C(OCC)(=O)C.O>CS(C)=O>[C:17]([C:4]1[C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=[C:2]([F:19])[N:3]=1)#[N:18]

Participants

Conditions

Temperature: 112.5 °C

Procedure

In 86 mL of dimethyl sulfoxide was dissolved 4.3 g of N-(5-bromo-3-cyano-2-pyrazinyl)benzamide. After adding 8.3 g of potassium fluoride, the mixture thus obtained was stirred at 110-115° C. for one hour. The reaction mixture was returned to room temperature, a mixture of 100 mL of ethyl acetate and 200 mL of water was added, and the organic layer was separated. The organic layer thus obtained was washed successively with water and saturated aqueous solution of sodium chloride, treated with active charcoal and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent: toluene:ethyl acetate=5:1] to obtain 0.47 g of N-(3-cyano-5-fluoro-2-pyrazinyl)benzamide as a white-colored solid product.

Workup

customthe mixture thus obtained
customwas returned to room temperature
additionwas added
customthe organic layer was separated
customThe organic layer thus obtained
washwas washed successively with water and saturated aqueous solution of sodium chloride
additiontreated with active charcoal
dry with materialdried on anhydrous magnesium sulfate
customthe solvent was removed under reduced pressure
customThe residue thus obtained
customwas purified by silica gel column chromatography [eluent: toluene:ethyl acetate=5:1]

Sources & evidence

ORD record: ord-e816d635e3c2497f86902632a22136ef
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800629B2

Reaction notes

Loading…