Pivalamidine hydrochloride → HCID 178441866, compound

HRID 1050938Notes

Reaction equation

HRID 1050938 reaction equation
[CH:1]1([C:5](=O)[CH2:6][C:7]([O:9]C)=O)[CH2:4][CH2:3][CH2:2]1.[CH3:12][C:13]([CH3:18])([CH3:17])[C:14]([NH2:16])=[NH:15].C[O-].[Na+]>CO>[C:13]([C:14]1[N:16]=[C:7]([OH:9])[CH:6]=[C:5]([CH:1]2[CH2:2][CH2:3][CH2:4]2)[N:15]=1)([CH3:18])([CH3:17])[CH3:12]

Participants

5

Reactant 3

HCID 431752Pivalamidine hydrochlorideHCID 10942334Sodium MethoxideHCID 52911251Methyl 3-cyclobutyl-3-oxopropanoate

Product 1

HCID 178441866HCID 178441866, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-cyclobutyl-3-oxo-propanoate (4.3 g, 27.53 mmol) and 2,2-dimethylpropanamidine (2.3 g, 22.10 mmol) was stirred in dry MeOH (50 mL) and NaOMe (5.0 g, 92 mmol) was added in portions at 10° C. The suspension was stirred at room temperature overnight. The reaction mixture was concentrated to roughly half of the volume and filtered. The filtrate was extracted with water and DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was stirred with acetone and the precipitate collected, dried under vacuum to give the title compound (3.15 g, 15.27 mmol, 66%).

Workup

  1. concentrationThe reaction mixture was concentrated to roughly half of the volume
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with water and DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. stirringThe residue was stirred with acetone
  9. customthe precipitate collected
  10. customdried under vacuum

Sources & evidence

ORD record
ord-2c992299056f488e84711f461d94cef4
Source dataset
uspto-grants-2016_07
Patent number
US09388141B2

Reaction notes

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