Ethyl Acetate → 5-Chloro-1-(3-fluoro-5-methylbenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide

HRID 1260880Notes

Reaction equation

HRID 1260880 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:12][CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([F:21])[CH:15]=1.C(OCC)(=O)C>CN(C=O)C>[BrH:12].[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:19]=[C:18]([CH3:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27784513-Fluoro-5-methylbenzyl bromideHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 686616225-Chloro-1-(3-fluoro-5-methylbenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromideYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-amino-5-chloronicotinamide (150 mg) and 1-(bromomethyl)-3-fluoro-5-methylbenzene (270 mg) in DMF (3 ml) was stirred at 100° C. for 24 hr. After cooling to room temperature, ethyl acetate was added, and the precipitated crystals were filtered and recrystallized to give the title compound (139 mg).

Workup

  1. filtrationthe precipitated crystals were filtered
  2. customrecrystallized

Sources & evidence

ORD record
ord-eee8f1bdd6fe409ba3a510730a761f4d
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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