2-(Bromomethyl)-4-chlorobenzonitrile → 5-Chloro-1-(5-chloro-2-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1260900Notes

Reaction equation

HRID 1260900 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]>CN(C)C=O>[ClH:11].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:13][C:14]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=2[C:16]#[N:17])[CH:9]=1

Participants

4

Reactant 2

HCID 126680532-(Bromomethyl)-4-chlorobenzonitrileHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 686622665-Chloro-1-(5-chloro-2-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 1.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-4-chlorobenzonitrile (0.31 g), and the mixture was stirred at 100° C. for 14 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2-4:1). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (2 mg).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2-4:1)
  7. addition2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature
  8. customthe obtained precipitate was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-60be1d7ba5074f429f5f7ddd946e1ee2
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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