Dimethylformamide → HCID 44476495, compound

HRID 1693270Notes

Reaction equation

HRID 1693270 reaction equation
[OH2:1].[SH-:2].[Na+].CC1C=CC(S(O[CH:15]([C:53]#[N:54])[CH2:16][C:17]2[C:25]3[C:20](=[N:21][C:22]([N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[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.[CH3:55]N(C)C=O>>[C:53]([CH:15]1[CH2:16][C:17]2[C:25]3[C:20]([N:19]([CH2:42][C:43]4[C:48]([CH3:49])=[C:47]([O:1][CH3:55])[C:46]([CH3:52])=[CH:45][N:44]=4)[N:18]=2)=[N:21][C:22]([N:27]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[C:35]([O:37][C:38]([CH3:39])([CH3:40])[CH3:41])=[O:36])=[N:23][C:24]=3[S:2]1)#[N:54]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 16211346Sodium hydrosulfide hydrateHCID 59311568HCID 59311568, compound

Product 1

HCID 44476495HCID 44476495, compoundYield 81%

Procedure

Sodium bisulfide monohydrate (58 mg) was added to a mixture composed 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-cyanoethyl 4-methylbenzenesulfonate (450 mg) and dehydrated N,N-dimethylformamide (8 mL) under cooling in an ice bath. Then, the ice bath was removed and the mixture was stirred for one hour. Potassium carbonate (84 mg) was added to the reaction mixture, followed by further stirring for 30 minutes. Water (100 mL) was added to the reaction mixture, 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. The resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane) to obtain the title compound (277 mg, 81%) as an oil.

Workup

  1. temperatureunder cooling in an ice bath
  2. customThen, the ice bath was removed
  3. additionPotassium carbonate (84 mg) was added to the reaction mixture
  4. stirringby further stirring for 30 minutes
  5. additionWater (100 mL) was added to the reaction mixture
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ebde14c0cb6d4d45a6aa1aa453cdf873
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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