4-{[5-(Azidomethyl)-1,6-diethyl-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}-1-piperidinecarboxamide → 4-{[5-(Aminomethyl)-1,6-diethyl-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}-1-piperidinecarboxamide
Reaction equation
[N:1]([CH2:4][C:5]1[C:6]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([NH2:27])=[O:26])[CH2:21][CH2:20]2)=[C:7]2[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:8]2=[N:9][C:10]=1[CH2:11][CH3:12])=[N+]=[N-]>C(O)C>[NH2:1][CH2:4][C:5]1[C:6]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25]([NH2:27])=[O:26])[CH2:21][CH2:20]2)=[C:7]2[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:8]2=[N:9][C:10]=1[CH2:11][CH3:12]Participants
3
Procedure
10% Palladium on carbon (0.65 g), in a flask flushed with nitrogen, was treated with water (about 2 ml), ethanol (20 ml) and a suspension of 4-{[5-(azidomethyl)-1,6-diethyl-1H-pyrazolo[3,4-b]pyridin-4-yl]amino}-1-piperidinecarboxamide (4.1 g, 11.0 mmol, e.g. which can be as prepared in Intermediate 16) in ethanol (100 ml). Additional ethanol (200 ml) was used to wash the suspension into the flask. The suspension was stirred under an atmosphere of hydrogen for 21 hours. The mixture was filtered through celite to remove catalyst, and the filtrate was evaporated to dryness to give the title compound as a grey foam (3.8 g). LCMS m/z 346 [MH+]; TRET=about 1.66 min.
Workup
- custom10% Palladium on carbon (0.65 g), in a flask flushed with nitrogen
- additionwas treated with water (about 2 ml), ethanol (20 ml)
- washto wash the suspension into the flask
- filtrationThe mixture was filtered through celite
- customto remove catalyst
- customthe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-a52b350868204e549e4839a9124490e3
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003663B2
Reaction notes
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