Potassium Carbonate → HCID 10273711, compound

HRID 229677Notes

Reaction equation

HRID 229677 reaction equation
N[C:2]1[CH:3]=[C:4]([N:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]#[N:27])[C:9]2=[O:28])[CH:5]=[CH:6][CH:7]=1.[S-:29][C:30]#[N:31].[NH4+:32].BrBr.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C.C(O)(=O)C>[NH2:31][C:30]1[S:29][C:2]2[CH:3]=[C:4]([N:8]3[CH:13]=[C:12]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=4)[CH:11]=[C:10]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:26]#[N:27])[C:9]3=[O:28])[CH:5]=[CH:6][C:7]=2[N:32]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 15666Ammonium thiocyanateHCID 24408BromineHCID 9925276HCID 9925276, compound

Product 1

HCID 10273711HCID 10273711, compoundYield 33.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of 1-(3-aminophenyl)-3-(2-cyanophenyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one and 63 mg of ammonium thiocyanate were added to 2 ml of acetic acid. The mixture was stirred at room temperature for 1 hour, to which 0.022 ml of bromine was added, and further stirred for 1 hour. The reaction mixture was distributed into the ethyl acetate and water layers, and neutralized with 20% aqueous solution of potassium carbonate. The organic layer was washed with water, dried and concentrated, and the residue was refined by silica gel chromatography (ethyl acetate/hexane-based solvent), to obtain 58 mg of the subject compound.

Workup

  1. additionwas added
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e33d480d449457ab31832ce683e027c
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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