Trifluoroacetic acid → HCID 58097152, compound

HRID 1897936Notes

Reaction equation

HRID 1897936 reaction equation
[OH:1][C:2]1([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[N:17]=2)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[S:24]1[CH:25]=[CH:26][N:27]=[C:23]1[NH:22][C:18]1[N:17]=[C:16]([CH2:15][C:2]2([OH:1])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86649623HCID 86649623, compound

Product 1

HCID 58097152HCID 58097152, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5.9 mg of tert-butyl 4-hydroxy-4-((6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)piperidine-1-carboxylate in 1 ml of chloroform was added 0.5 ml of trifluoroacetic acid at 0° C., followed by stirring the reaction mixture at 0° C. for 2 hours. The reaction mixture was concentrated in vacuo, basified with saturated aqueous sodium bicarbonate solution, and extracted with chloroform. The resulting chloroform layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to give the title compound as a brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. extractionextracted with chloroform
  3. dry with materialThe resulting chloroform layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c2fd01fdf56d458abd121653e8948858
Source dataset
uspto-grants-2013_08
Patent number
US08519136B2

Reaction notes

Loading…