2-Dimethylaminopyridine → HCID 15280158, compound

HRID 1735687Notes

Reaction equation

HRID 1735687 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([CH:7]([CH3:9])[CH3:8])[C:3]=1[C:10]([NH2:12])=[O:11].CN(C1C=CC=CN=1)C.[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:25][CH:24]([CH3:26])[CH2:23][C:22]([NH:1][C:2]1[O:6][N:5]=[C:4]([CH:7]([CH3:8])[CH3:9])[C:3]=1[C:10]([NH2:12])=[O:11])=[O:27]

Participants

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 66054Isovaleryl chlorideHCID 15280157HCID 15280157, compound

Product 1

HCID 15280158HCID 15280158, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 1140TolueneSolvent2×

Procedure

1.7 g of 5-amino-3-isopropylisoxazole-4-carboxamide in a mixture of 40 ml of toluene and 40 ml of pyridine are initially taken together with a pinch of dimethylaminopyridine, and a solution of 2.5 g of isovaleroyl chloride in 20 ml of toluene is added. Stirring is carried out for 16 hours at room temperature, after which the solution is evaporated to dryness and the residue is stirred with ethyl acetate. The organic phase is then extracted with aqueous hydrochloric acid and sodium bicarbonate solution, dried and evaporated down. Purification is effected by chromatography over silica gel (cyclohexane/ethyl acetate).

Workup

  1. customafter which the solution is evaporated to dryness
  2. stirringthe residue is stirred with ethyl acetate
  3. extractionThe organic phase is then extracted with aqueous hydrochloric acid and sodium bicarbonate solution
  4. customdried
  5. customevaporated down
  6. customPurification

Sources & evidence

ORD record
ord-c8cf2a34b386465b85e5ac1be92e58d3
Source dataset
uspto-grants-1996_07
Patent number
US05538939

Reaction notes

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