Trifluoroacetic acid → HCID 45111427, compound

HRID 473345Notes

Reaction equation

HRID 473345 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[CH:21]=[CH:20][N:19]=[CH:18][C:17]=3[C:16]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:16]2[C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67330403HCID 67330403, compound

Product 1

HCID 45111427HCID 45111427, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(4-Chlorophenyl)-pyrazolo[4,3-c]pyridin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester (200 mg, 0.48 mmol) was dissolved in DCM (5 mL) and TFA (5 mL) was added. The reaction mixture was stirred at room temperature for 30 min. The solvents were removed in vacuo and the residue was dissolved in 1 M aq Na2CO3 solution (50 mL) and extracted with DCM (3×50 mL). The combined organic layers were dried (MgSO4) and the solvents removed in vacuo. The residue was purified by reverse phase HPLC (YMC ODS-A 100×20 mm, 5 μm, 25 mL/min, gradient 40% to 100% (over 7 min) then 100% (3 min) MeOH in 10% MeOH/water) to give 3-(4-chlorophenyl)-1-piperidin-4-yl-1H-pyrazolo[4,3-c]-pyridine (76 mg, 50.2%) as a white solid.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in 1 M aq Na2CO3 solution (50 mL)
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customThe residue was purified by reverse phase HPLC (YMC ODS-A 100×20 mm, 5 μm, 25 mL/min, gradient 40% to 100% (over 7 min)

Sources & evidence

ORD record
ord-a13f9e5f6cee4d83ad5bb38b76864285
Source dataset
uspto-grants-2014_01
Patent number
US08633318B2

Reaction notes

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