Trifluoroacetic acid → HCID 57646934, compound

HRID 1887102Notes

Reaction equation

HRID 1887102 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:16]([Cl:26])=[C:17]3[C:22](=[CH:23][C:24]=2[Cl:25])[CH:21]=[N:20][CH:19]=[CH:18]3)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:26][C:16]1[C:15]([O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[C:24]([Cl:25])[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][N:20]=[CH:21]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57647072HCID 57647072, compound

Product 1

HCID 57646934HCID 57646934, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

150 mg 4-(5,7-Dichloro-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (377, already partially deprotected) were dissolved in 10 ml of dichloromethane and 1 ml of trifluoroacetic acid is added at 0° C. The solution is stirred for 2 h at room temperature. For working up, 50 ml Dichloromethane were added and the solution was washed with saturated NaHCO3-solution. The layers were separated and the aqueous phase was extracted once with Dichloromethane. The combined organic layers were again washed with saturated NaHCO3-solution, dried with MgSO4 and evaporated. The residue was purified by preparative HPLC. The product fractions were evaporated and the residue dissolved in 2 N HCl. After evaporation, the title compound was isolated as HCl-salt. Rt=0.90 min (Method #2). Detected mass: 297.1/299.1 (M+H+).

Workup

  1. washthe solution was washed with saturated NaHCO3-solution
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted once with Dichloromethane
  4. washThe combined organic layers were again washed with saturated NaHCO3-solution
  5. dry with materialdried with MgSO4
  6. customevaporated
  7. customThe residue was purified by preparative HPLC
  8. customThe product fractions were evaporated
  9. dissolutionthe residue dissolved in 2 N HCl
  10. customAfter evaporation

Sources & evidence

ORD record
ord-a8663b8b2fd0480bbc9ccf4771acf7fd
Source dataset
uspto-grants-2013_08
Patent number
US08501736B2

Reaction notes

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