HCID 59568648, compound → HCID 59568649, compound

HRID 2281335Notes

Reaction equation

HRID 2281335 reaction equation
[C:1]([C:3]1[C:4]([O:25][CH3:26])=[CH:5][C:6]([CH:9]([OH:24])[CH2:10][N:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)=[N:7][CH:8]=1)#[N:2]>C(O)(C(F)(F)F)=O>[OH:24][CH:9]([C:6]1[N:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([O:25][CH3:26])[CH:5]=1)[CH2:10][N:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

3

Reactant 1

HCID 59568648HCID 59568648, compound

Product 1

HCID 59568649HCID 59568649, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The slower eluting isomer of tert-Butyl 4-[2-(5-cyano-4-methoxy-2-pyridyl)-2-hydroxy-ethyl]piperazine-1-carboxylate (1.0 g, 2.76 mmol) was dissolved in 5 mL of TFA and stirred at room temperature for 2 hours. The mixture was concentrated to ¼ the original volume and diluted with 10 mL of diethyl ether. The precipitate was filtered and dried under high vacuum to offer amine TFA salt. This intermediate was diluted with 5% aqueous sodium bicarbonate with follow up addition of 10 N NaOH to bring the pH of extraction above 10. The aqueous layer was extracted with ethyl acetate. The organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure to provide the product (Isomer B).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with 10 mL of diethyl ether
  3. filtrationThe precipitate was filtered
  4. customdried under high vacuum
  5. additionThis intermediate was diluted with 5% aqueous sodium bicarbonate
  6. additionwith follow up addition of 10 N NaOH
  7. extractionthe pH of extraction above 10
  8. extractionThe aqueous layer was extracted with ethyl acetate
  9. dry with materialThe organic layers were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customto provide the product (Isomer B)

Sources & evidence

ORD record
ord-db96a86491fa44ac861c4be48c2ad7cb
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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