Potassium Carbonate → HCID 10470894, compound

HRID 750727Notes

Reaction equation

HRID 750727 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[NH2:10][C:11]1[C:19]2[C:14](=[N:15][C:16](N3CCNCC3)=[CH:17][C:18]=2[CH2:20]CC)[S:13][C:12]=1[C:29]([NH2:31])=[O:30].C(=O)([O-])[O-:33].[K+].[K+].[H-].[Na+]>CN(C=O)C>[NH2:10][C:11]1[C:19]2[C:14](=[N:15][C:16]([O:33][CH2:3][C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)=[CH:17][C:18]=2[CH3:20])[S:13][C:12]=1[C:29]([NH2:31])=[O:30]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 745704-(Chloromethyl)pyridinium chlorideHCID 11723489HCID 11723489, compound

Product 1

HCID 10470894HCID 10470894, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

4-Chloromethylpyridine hydrochloride (57.0 mg, 0.34 mmol) was combined with 50 mg of 4-methyl-mercaptopyridone intermediate (prepared analogous to Example 1) (0.22 mmol), and potassium carbonate (95.0 mg, 0.68 mmol) in DMF (1.0 mL) in a flame-dried pressure tube, under Ar. The tube was sealed and heated at 70° C. for 45 min. TLC showed complete disappearance of starting material and a new spot formed. The reaction was cooled to 0° C., and sodium hydride (9.0 mg, 0.23 mmol) was added. The reaction was warmed to room temperature and stirred for 30 min, after which it was cooled in an ice bath and quenched with aqueous sodium bicarbonate (saturated). The resulting mixture was extracted twice with EtOAc. The organic layers were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to afford 65.8 mg of the crude product which was purified via automated flash silica to afford 41.8 mg (0.13 mmol, 59% yield) of the title compound.

Workup

  1. customThe tube was sealed
  2. customa new spot formed
  3. temperatureThe reaction was cooled to 0° C.
  4. temperatureThe reaction was warmed to room temperature
  5. temperatureafter which it was cooled in an ice bath
  6. customquenched with aqueous sodium bicarbonate (saturated)
  7. extractionThe resulting mixture was extracted twice with EtOAc
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford 65.8 mg of the crude product which
  13. customwas purified via automated flash silica

Sources & evidence

ORD record
ord-5b3ee0fa71c54f8eab15a72a31343506
Source dataset
uspto-grants-2008_07
Patent number
US07405225B2

Reaction notes

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