1-(2-Pyridyl)piperazine → HCID 178481610, compound

HRID 538072Notes

Reaction equation

HRID 538072 reaction equation
[C:1]([N:4]([CH3:25])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:14][CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=O)[CH2:18][CH2:17]1)=[O:13])([OH:3])=O.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1>O=S(Cl)Cl>[CH3:25][N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:11][C:12](=[O:13])[N:14]([CH2:15][C@H:16]2[CH2:17][CH2:18][C@H:19]([C:22]([N:35]3[CH2:36][CH2:37][N:32]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=4)[CH2:33][CH2:34]3)=[O:24])[CH2:20][CH2:21]2)[C:1]1=[O:3]

Participants

4

Reactant 2

HCID 944591-(2-Pyridyl)piperazineHCID 178485955HCID 178485955, compound

Product 1

HCID 178481610HCID 178481610, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of trans-4-({2-[2-(Carboxy-methyl-amino)-phenyl]-acetylamino}-methyl)-cyclohexanecarboxylic acid (0.14 mmol, 0.05 g) in SOCl2 (0.8 mL) was heated under reflux for 1.5 hours. The solvent was removed under reduced pressure and the residue was put under vacuum overnight. Then crude product was diluted with 5 ml of dry DCM. 1 ml of this stock solution was transferred in a glass vial. 39 μL (0.27 mmol) of 1-Pyridin-2-yl-piperazine were added and the reaction mixture was left stirring at room temperature under argon over night. The solvent was removed under vacuum and the crude purified by preparative HPLC (Method d) to give 26 mg of the titled compound (yield 39%).

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customThe solvent was removed under reduced pressure
  3. customwas put under vacuum overnight
  4. additionThen crude product was diluted with 5 ml of dry DCM
  5. waitthe reaction mixture was left
  6. customThe solvent was removed under vacuum
  7. customthe crude purified by preparative HPLC (Method d)

Sources & evidence

ORD record
ord-00113549fdf1454e82ec4b91fa5a17d4
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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