Trifluoroacetic acid → 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 387583Notes

Reaction equation

HRID 387583 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:17]=2[N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[N:12](CC2C=CC(OC)=CC=2)[N:11]=1>C(Cl)Cl>[CH3:8][O:9][C:10]1[C:18]2[C:13](=[N:14][CH:15]=[C:16]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:17]=2[N:19]2[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:12][N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68759898tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 687585923-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridineYield 118.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to tert-butyl 4-(3-methoxy-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.098 g, 0.185 mmol) in DCM (2 mL) and stirred at room temperature for 2 hours. The reaction mixture was then concentrated to dryness. The resulting residue was dissolved in TFA (2.85 mL, 37.01 mmol) and heated at 100° C. in a sealed tube for 5 hours. The reaction mixture was again concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), followed by the addition of HCl in ether (2 mL, 2N). The resulting solid was collected by filtration to give 3-methoxy-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine (0.068 g, 96%). MS APCI (+) m/z 310.1 detected.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. temperatureheated at 100° C. in a sealed tube for 5 hours
  3. concentrationThe reaction mixture was again concentrated to dryness
  4. dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
  5. additionfollowed by the addition of HCl in ether (2 mL, 2N)
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-cc4346c5c6b34f7db5a13e4f47795f6f
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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