Dichloromethane → HCID 68756410, compound

HRID 387591Notes

Reaction equation

HRID 387591 reaction equation
C(O)(C(F)(F)F)=O.COC1C=CC(C[N:15]2[C:19]3=[N:20][CH:21]=[C:22]([C:37]([F:40])([F:39])[F:38])[C:23]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[C:18]3[CH:17]=[N:16]2)=CC=1.C(Cl)[Cl:44]>>[ClH:44].[ClH:44].[N:24]1([C:23]2[C:22]([C:37]([F:39])([F:40])[F:38])=[CH:21][N:20]=[C:19]3[NH:15][N:16]=[CH:17][C:18]=23)[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acid2×HCID 68757535HCID 68757535, compound

Product 1

HCID 68756410HCID 68756410, compoundYield 94%

Procedure

TFA (0.5 mL) was added to a solution of tert-butyl 4-(1-(4-methoxybenzyl)-5-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.114 g, 0.232 mmol) in DCM (2 mL) and stirred at room temperature for 1 hour. The reaction was then concentrated to dryness. The resulting residue was dissolved in TFA (1.79 mL, 23.2 mmol) and heated at 65° C. for 2 hours. The reaction was again 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 4-(piperazin-1-yl)-5-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.075 g, 94%). MS APCI (+) m/z 272.0 detected.

Workup

  1. concentrationThe reaction was then concentrated to dryness
  2. temperatureheated at 65° C. for 2 hours
  3. concentrationThe reaction was again 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-1ab3d91542524edea601f8733a9aee4e
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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