Piperidine-1-carboxamidine → 2-(4-Ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

HRID 1399736Notes

Reaction equation

HRID 1399736 reaction equation
[N:1]1([C:7](=[NH:9])[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:10]([CH:14]([CH:20]([CH2:26][CH2:27][CH3:28])[C:21](OCC)=[O:22])[C:15]([O:17]CC)=[O:16])(=O)[CH2:11][CH3:12].C[O-].[Na+]>CO>[CH2:27]([C:26]1[N:9]=[C:7]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[NH:8][C:21](=[O:22])[C:20]=1[CH:14]([CH2:10][CH2:11][CH3:12])[C:15]([OH:17])=[O:16])[CH3:28]

Participants

5

Reactant 3

HCID 205051Piperidine-1-carboxamidineHCID 10942334Sodium MethoxideHCID 86665656Diethyl 2-propionyl-3-propylsuccinate

Product 1

HCID 1363461602-(4-Ethyl-6-oxo-2-(piperidin-1-yl)-1,6-dihydropyrimidin-5-yl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of piperidine-1-carboximidamide (dimer complexated with H2SO4) (1 g; 7.86 mmol) and diethyl 2-propionyl-3-propylsuccinate (2.14 g; 7.86 mmol) in methanol (8 mL) was slowly added a solution of sodium methoxide in methanol (25% w:w) (3.60 mL; 15.72 mmol) and the reaction was heated under reflux for 18 h. The mixture was concentrated under reduced pressure and the curde residue was used as such in the next reaction.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 18 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customsuch in the next reaction

Sources & evidence

ORD record
ord-70610a653ff64ff98d8e9671db5dfcd4
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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