2-Amino-5-chloronicotinamide → 1-[3-(Aminocarbonyl)-5-chlorobenzyl]-5-chloro-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide

HRID 1260868Notes

Reaction equation

HRID 1260868 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:15]=[C:16]([CH:20]=[C:21]([Cl:23])[CH:22]=1)[C:17]([NH2:19])=[O:18]>CN(C)C=O.C(OCC)(=O)C>[BrH:12].[NH2:19][C:17]([C:16]1[CH:15]=[C:14]([CH:22]=[C:21]([Cl:23])[CH:20]=1)[CH2:13][N:10]1[CH:9]=[C:8]([Cl:11])[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2]1=[NH:1])=[O:18]

Participants

5

Reactant 2

HCID 668768832-Amino-5-chloronicotinamideHCID 686616453-(Bromomethyl)-5-chlorobenzamide

Product 1

HCID 686620451-[3-(Aminocarbonyl)-5-chlorobenzyl]-5-chloro-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromideYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(Step 3) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-chlorobenzamide (0.26 g) obtained in Step 2, and the mixture was stirred at 100° C. for 3 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (110 mg).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customThe obtained precipitate was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-dd7924e3a7564cf6a95896ac8fea6de4
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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