Piperazine → HCID 178440761, compound

HRID 494022Notes

Reaction equation

HRID 494022 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:14]3[C:15](Cl)=[N:16][CH:17]=[CH:18][C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(OCC)(=O)C>CS(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:14]3[C:15]([N:21]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]4)=[N:16][CH:17]=[CH:18][C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 4837Piperazine2×HCID 8857Ethyl AcetateHCID 178440760HCID 178440760, compound

Product 1

HCID 178440761HCID 178440761, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of the chloroimidazopyridine 4 (0.75 g, 2.6 mmol) and piperazine (6.8 g, 79 mmol) in DMSO (15 mL) was heated to 140° C. for 3 hours. During this time, the reaction mixture was gently swirled every 30 minutes to redissolve piperazine on the upper walls of the flask. After cooling to room temperature, ethyl acetate (150 mL) was added and the solution was washed with water (3×100 mL), dried over MgSO4, and evaporated to leave a yellow powder (0.75 g, 86%). LC/MS (method A); Rt=0.90 minutes, [M+H]+=336, purity>99%.

Workup

  1. washthe solution was washed with water (3×100 mL)
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-1b28962aa0b145c39cec6dc032f4be71
Source dataset
uspto-grants-2009_05
Patent number
US07538113B2

Reaction notes

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