Potassium Carbonate → HCID 9994643, compound

HRID 1063101Notes

Reaction equation

HRID 1063101 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-a0873d0e730b4ed4946b9490363aaa6c
Source dataset
uspto-grants-2005_11
Patent number
US06964956B2

Reaction notes

Loading…