2-Amino-2,3-dimethylbutanamide → HCID 178439576, compound

HRID 358848Notes

Reaction equation

HRID 358848 reaction equation
[CH3:1][O-].[Na+].C([O:6][C:7]([C:9]1[C:14](C(OCC)=O)=[CH:13][CH:12]=[C:11]([CH:20]2[CH2:22][CH2:21]2)[N:10]=1)=[O:8])C.[NH2:23][C:24]([CH3:31])([CH:28]([CH3:30])[CH3:29])[C:25]([NH2:27])=[O:26]>CO.C(O)C>[CH:20]1([C:11]2[NH:10][C:9]([C:1]3[NH:23][C:24]([CH:28]([CH3:30])[CH3:29])([CH3:31])[C:25](=[O:26])[N:27]=3)([C:7]([OH:6])=[O:8])[CH:14]=[CH:13][CH:12]=2)[CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 10942334Sodium MethoxideHCID 142803436-Cyclopropylpyridine-2,3-dicarboxylic acid diethyl ester

Product 1

HCID 178439576HCID 178439576, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

10 g of 30% sodium methoxide in methanol are added to a solution of 6 g of 6-cyclopropylpyridine-2,3-dicarboxylic acid diethyl ester and 3 g of 2-amino-2,3-dimethylbutyramide in 100 ml of ethanol and the reaction mixture is boiled under reflux for 3 hours. It is then concentrated, the residue is dissolved in a small amount of water, and the solution is saturated with sodium chloride. The pH is then adjusted to 4 with concentrated hydrochloric acid and the solution is extracted three times with 150 ml of ethyl acetate each time. The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue crystallises from ether/hexane 1:2. In this manner 4 g of 6-cyclopropyl-2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-pyridinecarboxylic acid having a melting point of 118°-121° are obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationIt is then concentrated
  3. dissolutionthe residue is dissolved in a small amount of water
  4. extractionthe solution is extracted three times with 150 ml of ethyl acetate each time
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue crystallises from ether/hexane 1:2

Sources & evidence

ORD record
ord-46dcbf34d7e349ff9246061a2d2f5548
Source dataset
uspto-grants-1991_03
Patent number
US04997947

Reaction notes

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