Potassium Carbonate → HCID 21846964, compound

HRID 619725Notes

Reaction equation

HRID 619725 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])[CH2:31][CH2:32][CH3:33]>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])[CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110519635-IsoquinolinethiolHCID 21846938HCID 21846938, compound

Product 1

HCID 21846964HCID 21846964, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °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)butane amide 750 mg (3.1 mmol) were added, and the mixture was heated with stirring at 90° C. for 6 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate-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]butanamide 150 mg (12.9%).

Workup

  1. temperaturethe mixture was heated
  2. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate-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-2887da33b6c542ac9decbed01f415592
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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