Triethylamine → HCID 59592761, compound

HRID 2261011Notes

Reaction equation

HRID 2261011 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:12])[N:10]=[CH:11][C:6]2=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:4]=1.CCN(CC)CC.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CN(C=O)C>[CH3:12][N:9]1[C:7]2=[N:8][C:3]([CH2:2][N:33]3[CH2:34][CH2:35][N:30]([CH3:29])[CH2:31][CH2:32]3)=[CH:4][C:5]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=3)=[C:6]2[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 59592674HCID 59592674, compound2×

Product 1

HCID 59592761HCID 59592761, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

900 mg of 6-bromomethyl-1-methyl-4-(4-nitro-phenyl)-1H-pyrazolo[3,4-b]pyridine (Intermediate 17.7; 2.59 mmol, 1 eq.) were dissolved in 13.5 mL DMF and treated sequentially with 0.54 mL Et3N (3.9 mmol, 1.5 eq.) and 0.35 mL methyl piperazine (3.11 mmol, 1.2 eq.). The reaction mixture was heated to 90° C. for 45 min, partitioned between CH2Cl2 and water, the aqueous layer was re-extracted and the combined organic layers were dried and concentrated in vacuo to yield the crude piperazine product, which was used without further purification.

Workup

  1. custompartitioned between CH2Cl2 and water
  2. extractionthe aqueous layer was re-extracted
  3. customthe combined organic layers were dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04669d3a3ab94bfa9d2b755d3e5c4b69
Source dataset
uspto-grants-2010_12
Patent number
US07846928B2

Reaction notes

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