Trifluoroacetic acid → 5-cyclopropyl-1-(4-methoxybenzyl)-4-(piperazin-1-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine

HRID 387532Notes

Reaction equation

HRID 387532 reaction equation
[CH:1]1([C:4]2[C:5]([N:26]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]3)=[C:6]3[C:12]([C:13]([F:16])([F:15])[F:14])=[N:11][N:10]([CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([C:4]2[C:5]([N:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)=[C:6]3[C:12]([C:13]([F:14])([F:16])[F:15])=[N:11][N:10]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68765568HCID 68765568, compound

Product 1

HCID 687557085-cyclopropyl-1-(4-methoxybenzyl)-4-(piperazin-1-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridineYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (270 mg, 0.5 mmol) was placed in DCM (8 mL) at room temperature. TFA (1.5 mL) was then added, and the reaction was stirred at room temperature for 1 hour and concentrated to dryness. The crude product was then azeotroped with toluene (3×) and then dried on a vac line for 1 hour to give the crude product 5-cyclopropyl-1-(4-methoxybenzyl)-4-(piperazin-1-yl)-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (0.2 g, 91% yield), which was used without further purification.

Workup

  1. concentrationconcentrated to dryness
  2. customThe crude product was then azeotroped with toluene (3×)
  3. customdried on a vac line for 1 hour

Sources & evidence

ORD record
ord-179da83bcfe94e3db5f3283db7c29cf5
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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