2-Amino-2,3-dimethylbutanamide → HCID 178439580, compound

HRID 358850Notes

Reaction equation

HRID 358850 reaction equation
CC(C)([O-])C.[K+].C(O[C:10]([C:12]1[C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=[C:14]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[N:13]=1)=O)C.[NH2:28][C:29]([CH3:36])([CH:33]([CH3:35])[CH3:34])[C:30]([NH2:32])=[O:31]>C1(C)C=CC=CC=1>[S:25]1[CH:26]=[CH:27][C:23]([C:14]2[N:13]=[C:12]([C:10]3[NH:28][C:29]([CH:33]([CH3:35])[CH3:34])([CH3:36])[C:30](=[O:31])[N:32]=3)[C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[CH:24]1

Participants

5

Reactant 3

HCID 97937732-Amino-2,3-dimethylbutanamideHCID 23665647Potassium tert-butoxideHCID 54221504HCID 54221504, compound

Product 1

HCID 178439580HCID 178439580, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

12 g of potassium tert.-butoxide are added to a solution of 14 g of 6-(thiophen-3-yl)-pyridine-2,3-dicarboxylic acid diethyl ester and 6 g of 2-amino-2,3-dimethyl- butyramide in 100 ml of dry toluene while stirring and the solution is heated at 80° C. for 5 hours. The reaction solution is then poured onto ice, the phases are separated and the aqueous phase is acidified with 10 ml of glacial acetic acid. After some time the above acid crystallises out and is filtered off with suction and dried. In this manner 13.5 g of 6-(thiophen-3-yl)-2-(5-isopropyl-5-methyl-4-oxo-imidazol-2-yl)-pyridine-3-carboxylic acid having a melting point of 253°-257° C. are obtained.

Workup

  1. additionThe reaction solution is then poured onto ice
  2. customthe phases are separated
  3. customAfter some time the above acid crystallises out and
  4. filtrationis filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-cf512ed7d25e4c498ac10272e7521869
Source dataset
uspto-grants-1991_03
Patent number
US04997947

Reaction notes

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