tert-butyl 4-(4-amino-1H-pyrazol-1-yl)piperidine-1-carboxylate → [3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-(1-piperidin-4-yl-1H-pyrazol-4-yl)-amine

HRID 1481251Notes

Reaction equation

HRID 1481251 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[N:10]=[N:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.C(OC([N:26]1[CH2:31][CH2:30][CH:29]([N:32]2[CH:36]=[C:35]([NH2:37])[CH:34]=[N:33]2)[CH2:28][CH2:27]1)=O)(C)(C)C>COCCO>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[C:6]3[N:7]=[C:2]([NH:37][C:35]4[CH:34]=[N:33][N:32]([CH:29]5[CH2:30][CH2:31][NH:26][CH2:27][CH2:28]5)[CH:36]=4)[N:3]=[CH:4][C:5]=3[N:10]=[N:9]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 27281520tert-butyl 4-(4-amino-1H-pyrazol-1-yl)piperidine-1-carboxylateHCID 897179715-Chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 71667041[3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-(1-piperidin-4-yl-1H-pyrazol-4-yl)-amine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A solution of 183 mg (0.70 mmol) 5-chloro-3-(4-methoxy-phenyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (from example 2) and 186 mg (0.70 mmol) 4-(4-amino-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester in 1.8 ml 2-methoxy-ethanol is stirred for 4 hours at 100° C. The reaction mixture is cooled to room temperature, concentrated under vacuum and the residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent giving two products:

Workup

  1. concentrationconcentrated under vacuum
  2. customthe residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent
  3. customgiving two products

Sources & evidence

ORD record
ord-a3e17c9577ca4e7787e12b1c840ffc72
Source dataset
uspto-grants-2016_08
Patent number
US09409914B2

Reaction notes

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