Potassium Carbonate → HCID 21846899, compound

HRID 619726Notes

Reaction equation

HRID 619726 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([SH:11])[C:5]=2[CH:4]=[CH:3][N:2]=1.C(=O)([O-])[O-].[K+].[K+].[NH2:18][C:19]1[CH:24]=[C:23](F)[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:20]=1[NH:29][C:30](=[O:34])[CH:31]([CH3:33])[CH3:32]>CN(C=O)C>[NH2:18][C:19]1[CH:24]=[C:23]([S:11][C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][N:2]=[CH:1]3)[C:22]([N+:26]([O-:28])=[O:27])=[CH:21][C:20]=1[NH:29][C:30](=[O:34])[CH:31]([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110519635-IsoquinolinethiolHCID 21846992HCID 21846992, compound

Product 1

HCID 21846899HCID 21846899, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Isoquinolinethiol 500 mg (3.1 mmol) was dissolved in DMF 20 ml, potassium carbonate 1.29 g (9.3 mmol) and N1-(2-amino-4-fluoro-5-nitrophenyl)-2-methylpropane amide) 750 mg (3.1 mmol) were added, and the mixture was heated with stirring at 100° C. for 1 hour. The reaction mixture was concentrated under reduced pressure, ether was added to the resulting residue to crystallize. The crystals were collected and washed with methanol to obtain N1-[2-amino-4-(5-isoquinolylsulfanyl)-5-nitrophenyl]-2-methylpropanamide 380 mg (31.0%).

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure, ether
  3. additionwas added to the resulting residue
  4. customto crystallize
  5. customThe crystals were collected
  6. washwashed with methanol

Sources & evidence

ORD record
ord-0c21c1fb249d4efb8e6dbb35d3818d2f
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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