Potassium Carbonate → HCID 24811286, compound

HRID 1693273Notes

Reaction equation

HRID 1693273 reaction equation
[OH2:1].[SH-:2].[Na+].CC1C=CC(S(O[CH:15]([CH3:53])[CH2:16][C:17]2[C:25]3[C:20](=[N:21][C:22]([N:27](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:23][C:24]=3Cl)[N:19]([CH2:42][C:43]3[C:48]([CH3:49])=[C:47](OC)[C:46]([CH3:52])=[CH:45][N:44]=3)[N:18]=2)(=O)=O)=CC=1.[C:54](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:54][O:1][C:47]1[C:46]([CH3:52])=[CH:45][N:44]=[C:43]([CH2:42][N:19]2[C:20]3[C:25]4[C:17]([CH2:16][CH:15]([CH3:53])[S:2][C:24]=4[N:23]=[C:22]([NH2:27])[N:21]=3)=[N:18]2)[C:48]=1[CH3:49]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16211346Sodium hydrosulfide hydrateHCID 59311513HCID 59311513, compound

Product 1

HCID 24811286HCID 24811286, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium bisulfide monohydrate (3.8 mg) was added to a mixture of the above 2-{6-[bis(tert-butoxycarbonyl)amino]-4-chloro-1-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-1H-pyrazolo[3,4-d]pyrimidin-3-yl}-1-methylethyl 4-methylbenzenesulfonate (29 mg) and N,N-dimethylformamide (1 mL) under cooling in an ice bath, and the mixture was stirred for 20 minutes. Then, potassium carbonate (8.2 mg) was added and the ice bath was removed, followed by stirring for 10 hours. The reaction mixture was diluted with ethyl acetate and then sequentially washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane (2 mL). Then, trifluoroacetic acid (0.5 mL) was added and the mixture was stirred for two hours. The reaction mixture was concentrated under reduced pressure. Then, the resulting residue was dissolved in chloroform and sequentially washed with a saturated sodium bicarbonate solution and water. The organic layer was dried over anhydrous sodium sulfate and then filtered, and 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 (8.9 mg, 63%) as a solid.

Workup

  1. temperatureunder cooling in an ice bath
  2. customthe ice bath was removed
  3. stirringby stirring for 10 hours
  4. additionThe reaction mixture was diluted with ethyl acetate
  5. washsequentially washed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. dissolutionThe resulting residue was dissolved in dichloromethane (2 mL)
  10. additionThen, trifluoroacetic acid (0.5 mL) was added
  11. stirringthe mixture was stirred for two hours
  12. concentrationThe reaction mixture was concentrated under reduced pressure
  13. dissolutionThen, the resulting residue was dissolved in chloroform
  14. washsequentially washed with a saturated sodium bicarbonate solution and water
  15. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  16. filtrationfiltered
  17. concentrationthe filtrate was concentrated under reduced pressure
  18. customThe resulting residue was purified by silica gel thin-layer chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-f0c6b82f68024a33b403fce377aeac12
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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