Benzonitrile, 3-(bromomethyl)- → HCID 68661583, compound

HRID 1260853Notes

Reaction equation

HRID 1260853 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].[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH2:17][Br:18])#[N:13]>CN(C)C=O.C(OCC)(=O)C>[BrH:18].[Cl:11][C:8]1[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2](=[NH:1])[N:10]([CH2:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([C:12]#[N:13])[CH:15]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 668768832-Amino-5-chloronicotinamide

Product 1

HCID 68661583HCID 68661583, compoundYield 28.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
105 °C

Procedure

(Step 2) To a solution of 2-amino-5-chloronicotinamide (0.14 g) obtained in Step 1 in N,N-dimethylformamide (3 ml) was added 3-cyanobenzylbromide (0.19 g), and the mixture was stirred at 105° C. for 5 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 (85 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-6c47bdd7a69b469e8dcf978b38df0319
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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