Potassium Carbonate → HCID 67279889, compound

HRID 1693288Notes

Reaction equation

HRID 1693288 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH2:13][CH:14](CS([O-])(=O)=O)[C:15]=3[CH2:16][S:17][N:18]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:36][O:35][C:32]1[C:31]([CH3:37])=[CH:30][N:29]=[C:28]([CH2:27][N:25]2[N:24]=[C:12]3[CH:13]=[CH:14][C:15]4[CH2:16][S:17][N:18]=[C:9]([NH2:8])[C:10]([C:11]=43)=[N:26]2)[C:33]=1[CH3:34]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86641325HCID 86641325, compound

Product 1

HCID 67279889HCID 67279889, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture composed of 4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-ylmethanesulfonate of Example 35 (65 mg), dehydrated N,N-dimethylformamide (1 mL) and potassium carbonate (14 mg) was heated with stirring at 70° C. for six hours. The reaction mixture was cooled and a saturated sodium bicarbonate solution was added, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane (2 mL) and trifluoroacetic acid (1 mL) were added to the resulting residue, and the mixture was stirred at room temperature for one hour. After confirming that the raw material disappeared, the reaction mixture was concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with brine, and then dried over sodium sulfate and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol) to obtain the title compound (12.9 mg, 36%) as a solid.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. additionDichloromethane (2 mL) and trifluoroacetic acid (1 mL) were added to the resulting residue
  9. stirringthe mixture was stirred at room temperature for one hour
  10. concentrationthe reaction mixture was concentrated under reduced pressure
  11. additionA saturated sodium bicarbonate solution was added to the residue
  12. extractionfollowed by extraction with ethyl acetate
  13. washThe organic layer was washed with brine
  14. dry with materialdried over sodium sulfate
  15. filtrationfiltered
  16. concentrationThen, the filtrate was concentrated under reduced pressure
  17. customThe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e95d40fc84e1407d9572a72f637e84f0
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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