Dichloromethane → HCID 178438027, compound

HRID 387552Notes

Reaction equation

HRID 387552 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]([N:17]4[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]4)=[C:11]3[C:10](/[CH:36]=[CH:37]\[C:38]3[CH:39]=[N:40][N:41](CC4C=CC(OC)=CC=4)[CH:42]=3)=[N:9]2)=CC=1.C(O)(C(F)(F)F)=O.C(Cl)[Cl:62]>>[ClH:62].[NH:41]1[CH:42]=[C:38](/[CH:37]=[CH:36]\[C:10]2[C:11]3[C:12](=[N:13][CH:14]=[C:15]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:16]=3[N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)[NH:8][N:9]=2)[CH:39]=[N:40]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68757876(Z)-tert-butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 178438027HCID 178438027, compoundYield 97%

Procedure

(Z)-tert-Butyl 4-(1-(4-methoxybenzyl)-3-(2-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)vinyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.084 g, 0.12 mmol) in DCM (1 mL) was added TFA (0.5 mL) and stirred at room temperature for 1 hour. The solvent was removed. The residue was dissolved in TFA (4 ml) and heated at 78° C. (bath) in a sealed tube overnight. The solvent was removed. The residue was dissolved in DCM (0.5 mL) and 2N HCl in ether (1 mL) was added. The solid formed was collected by filtration to give (Z)-3-(2-(1H-pyrazol-4-yl)vinyl)-5-phenyl-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine hydrochloride (0.051 g, 97%) as a solid.

Workup

  1. customThe solvent was removed
  2. dissolutionThe residue was dissolved in TFA (4 ml)
  3. temperatureheated at 78° C. (bath) in a sealed tube overnight
  4. customThe solvent was removed
  5. dissolutionThe residue was dissolved in DCM (0.5 mL)
  6. addition2N HCl in ether (1 mL) was added
  7. customThe solid formed
  8. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-4b30c0c0a429468697a6989a987de1b0
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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