Trifluoroacetic acid → HCID 16222567, compound

HRID 1436009Notes

Reaction equation

HRID 1436009 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[C:21](=[O:25])[NH:20][CH:19]=[C:18]3[CH3:26])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:26][C:18]1[C:17]2[C:22](=[CH:23][CH:24]=[C:15]([O:14][C@H:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[CH:16]=2)[C:21](=[O:25])[NH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68875085HCID 68875085, compound

Product 1

HCID 16222567HCID 16222567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude (S)-3-(4-Methyl-1-oxo-1,2-dihydroisoquinolin-6-yloxy)piperidine-1-carboxylic acid tert-butyl ester was dissolved in 2 ml of DCM and excess TFA added (0.2 ml). After stirring for 2 hours the solvent was removed under reduced pressure and the residue dissolved in methanol and partially purified by ion exchange chromatography. Further purification by prep-HPLC gave (S)-4-methyl-6-(piperidin-3-yloxy)-2H-isoquinolin-1-one, El-MS: m/z=259.1 [M+H]+.

Workup

  1. customwas removed under reduced pressure
  2. dissolutionthe residue dissolved in methanol
  3. custompartially purified by ion exchange chromatography
  4. customFurther purification

Sources & evidence

ORD record
ord-c7ac76b020b9406cace6b6ed2200ad0f
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

Loading…