2-Amino-5-chloronicotinamide → HCID 68662148, compound

HRID 1260864Notes

Reaction equation

HRID 1260864 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:21]=[C:22]([Cl:24])[CH:23]=1)[C:17]([NH:19][CH3:20])=[O: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:15]=[C:16]([C:17]([NH:19][CH3:20])=[O:18])[CH:21]=[C:22]([Cl:24])[CH:23]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 668768832-Amino-5-chloronicotinamideHCID 68662124HCID 68662124, compound

Product 1

HCID 68662148HCID 68662148, compoundYield 29%

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-chloro-N-methylbenzamide (0.28 g), and the mixture was stirred at 100° C. for 12 hr. The reaction mixture was diluted with ethyl acetate. The solvent was removed, and the obtained precipitate was dissolved in methanol and crystallized from ethyl acetate. The obtained crystals were recrystallized from methanol-ethyl acetate to give the title compound (0.11 g).

Workup

  1. customThe solvent was removed
  2. dissolutionthe obtained precipitate was dissolved in methanol
  3. customcrystallized from ethyl acetate
  4. customThe obtained crystals were recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-17a50f0e07b54a4b83f05e7abc9af404
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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