3-(Bromomethyl)-5-fluorobenzonitrile → 5-Chloro-1-(3-cyano-5-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide

HRID 1260892Notes

Reaction equation

HRID 1260892 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:19]=[C:20]([F:22])[CH:21]=1)[C:17]#[N:18]>CN(C)C=O.C(OCC)(=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:21]=[C:20]([F:22])[CH:19]=[C:16]([C:17]#[N:18])[CH:15]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 666526293-(Bromomethyl)-5-fluorobenzonitrileHCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 686619425-Chloro-1-(3-cyano-5-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromideYield 20.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(Step 4) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-fluorobenzonitrile (0.29 g) obtained in Step 3, and the mixture was stirred at 100° C. for 14 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 (69 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-01a3d5c4c77442b3a321a6b6b846a90b
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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