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

HRID 387525Notes

Reaction equation

HRID 387525 reaction equation
[CH:1]1([C:4]2[C:5]([N:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)=[C:6]3[CH:12]=[N:11][N:10]([CH2:13][C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36].C(Cl)Cl>>[OH:41][C:35]([C:37]([F:40])([F:39])[F:38])=[O:36].[CH:1]1([C:4]2[C:5]([N:22]3[CH2:23][CH2:24][NH:25][CH2:26][CH2:27]3)=[C:6]3[CH:12]=[N:11][N:10]([CH2:13][C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[C:7]3=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68758042tert-butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 866472605-cyclopropyl-1-(4-methoxybenzyl)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine TFA saltYield 102%

Procedure

tert-Butyl 4-(5-cyclopropyl-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (275 mg, 0.593 mmol) was treated with 25% TFA/CH2Cl2 for 30 minutes. The solvent was then removed in vacuo, and the residue was evaporated from toluene (3×10 mL) to provide the crude 5-cyclopropyl-1-(4-methoxybenzyl)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine TFA salt (220 mg, 102% yield). LCMS (APCI+) m/z 364.1 (M+H)+, Rt=2.61 minutes.

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was evaporated from toluene (3×10 mL)

Sources & evidence

ORD record
ord-8e6e2addc11843dfb9822558251468e9
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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