Potassium Carbonate → HCID 9994643, compound

HRID 750728Notes

Reaction equation

HRID 750728 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7](N3CCNCC3)=[CH:8][C:9]=2[CH2:11]CC)[S:4][C:3]=1[C:20]([NH2:22])=[O:21].C([O-])([O-])=[O:24].[K+].[K+].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].[H-].[Na+]>CN(C=O)C>[CH3:34][O:33][C:31](=[O:32])[CH2:30][O:24][C:7]1[N:6]=[C:5]2[S:4][C:3]([C:20](=[O:21])[NH2:22])=[C:2]([NH2:1])[C:10]2=[C:9]([CH3:11])[CH:8]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 11723489HCID 11723489, compound

Product 1

HCID 9994643HCID 9994643, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of the 4-methyl-mercaptopyridone intermediate (prepared analogous to Example 1) (62 mg) and K2CO3 (70 mg) in DMF (1 mL) was added methyl bromoacetate (50 mg). The mixture was heated under Ar at 70° C. for 2 h. After cooling to 0° C., the mixture was treated with NaH (60%, 10 mg) and stirred at room temperature for 30 min. The mixture was then poured into ice —NH4Cl mixture, extracted with EtOAc, dried with Na2SO4 and concentrated. The residue was purified by preparative TLC, providing 5 mg of the title compound (white solid).

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with EtOAc
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7475d8935dbd42e39f3270c85d12d722
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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