Acetic Acid → HCID 117914081, compound

HRID 522282Notes

Reaction equation

HRID 522282 reaction equation
C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:30][CH2:31][CH2:32][N:33]1[C:37]2[N:38]=[C:39]([C:68]#[N:69])[N:40]=[C:41]([C:42]3[CH:63]=[CH:62][C:45]([O:46][CH2:47][CH2:48][CH:49]4[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:51][CH2:50]4)=[C:44]([C:64]([F:67])([F:66])[F:65])[CH:43]=3)[C:36]=2[CH:35]=[CH:34]1)(C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[C:68]([C:39]1[N:40]=[C:41]([C:42]2[CH:63]=[CH:62][C:45]([O:46][CH2:47][CH2:48][CH:49]3[CH2:54][CH2:53][N:52]([C:55]([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:56])[CH2:51][CH2:50]3)=[C:44]([C:64]([F:65])([F:67])[F:66])[CH:43]=2)[C:36]2[CH:35]=[CH:34][N:33]([CH2:32][CH2:31][OH:30])[C:37]=2[N:38]=1)#[N:69]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 131735525HCID 131735525, compound

Product 1

HCID 117914081HCID 117914081, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (0.1 mL) and a 1.0 M solution of tetrabutylammonium fluoride in THF (1 mL) were added to a solution of tert-butyl 4-(2-{4-[7-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate (390 mg) in THF (5 mL) at room temperature, and the mixture was stirred at the same temperature for 7 hours. After a saturated aqueous NaHCO3 solution was added to the reaction mixture, extraction thereof was performed using EtOAc, and the extract was washed with water and saturated brine. The organic layer was dried over MgSO4 and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hex:EtOAc=70:30 to 40:60), whereby tert-butyl 4-(2-{4-[2-cyano-7-(2-hydroxyethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-(trifluoromethyl)phenoxy}ethyl)piperidine-1-carboxylate (323 mg) was obtained as a colorless oil.

Workup

  1. washthe extract was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=70:30 to 40:60)

Sources & evidence

ORD record
ord-8e22b18f7f424fd3b45448fddb4c78fa
Source dataset
uspto-grants-2016_05
Patent number
US09328118B2

Reaction notes

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