Dichloromethane → HCID 68758725, compound

HRID 387586Notes

Reaction equation

HRID 387586 reaction equation
C(O)(C(F)(F)F)=O.[Br:8][C:9]1[C:10]([N:27]2[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]2)=[C:11]2[CH:17]=[N:16][N:15](CC3C=CC(OC)=CC=3)[C:12]2=[N:13][CH:14]=1.C(Cl)[Cl:41]>>[ClH:41].[ClH:41].[Br:8][C:9]1[C:10]([N:27]2[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]2)=[C:11]2[CH:17]=[N:16][NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 68760849tert-butyl 4-(5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate

Product 1

HCID 68758725HCID 68758725, compoundYield 70%

Procedure

TFA (0.5 mL) was added to a solution of tert-butyl 4-(5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.10 g, 0.20 mmol, see Example 1) in DCM (2 mL) and stirred at room temperature for 1 hour. The reaction mixture was then concentrated to dryness. The resulting residue was dissolved in TFA (3.067 mL, 39.81 mmol) and heated at 60° C. for 3 hours. The reaction was concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), and HCl in ether (2 mL, 2N) was added. The resulting solid was collected by filtration to give 5-bromo-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.050 g, 70%). MS APCI (+) m/z 282.0 detected.

Workup

  1. concentrationThe reaction mixture was then concentrated to dryness
  2. temperatureheated at 60° C. for 3 hours
  3. concentrationThe reaction was concentrated to dryness
  4. dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
  5. additionHCl in ether (2 mL, 2N) was added
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-1812778fc4164c91bec348d580b2c399
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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