Dichloromethane → 5-(3-fluorophenoxy)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride
Reaction equation
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[O:12][C:13]1[C:14]([N:31]2[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]2)=[C:15]2[CH:21]=[N:20][N:19](CC3C=CC(OC)=CC=3)[C:16]2=[N:17][CH:18]=1.C(Cl)[Cl:48]>>[ClH:48].[ClH:48].[F:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][CH:46]=1)[O:12][C:13]1[C:14]([N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[C:15]2[CH:21]=[N:20][NH:19][C:16]2=[N:17][CH:18]=1Participants
4
Procedure
TFA (0.5 mL) was added to tert-butyl 4-(5-(3-fluorophenoxy)-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (0.020 g, 0.0375 mmol) in DCM (2 mL) and stirred at room temperature for 1 hour. The reaction was concentrated to dryness. The resulting residue was dissolved in TFA (1 mL) and heated at 65° C. for 2 hours. The reaction was concentrated to dryness. The resulting residue was dissolved in DCM (0.5 mL), and HCl in ether (1 mL, 2N) was added. The reaction was concentrated to dryness to give 5-(3-fluorophenoxy)-4-(piperazin-1-yl)-1H-pyrazolo[3,4-b]pyridine dihydrochloride (0.014 g, 99%) as a solid. MS APCI (+) m/z 314.1 detected.
Workup
- concentrationThe reaction was concentrated to dryness
- dissolutionThe resulting residue was dissolved in TFA (1 mL)
- temperatureheated at 65° C. for 2 hours
- concentrationThe reaction was concentrated to dryness
- dissolutionThe resulting residue was dissolved in DCM (0.5 mL)
- additionHCl in ether (1 mL, 2N) was added
- concentrationThe reaction was concentrated to dryness
Sources & evidence
- ORD record
- ord-939796f2e9ac4f41977e194829c1c810
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372842B2
Reaction notes
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