Dimethylformamide → HCID 15451778, compound

HRID 1898795Notes

Reaction equation

HRID 1898795 reaction equation
[CH:1]1([CH:4]([N:6]2[C:15](=[O:16])[C:14]3[C:9](=[N:10][C:11](F)=[C:12]([CH3:17])[CH:13]=3)[C:7]2=[O:8])[CH3:5])[CH2:3][CH2:2]1.[O-]C#[N:21].[K+].CN(C=O)C>O>[CH:1]1([CH:4]([N:6]2[C:15](=[O:16])[C:14]3[C:9](=[N:10][C:11]([NH2:21])=[C:12]([CH3:17])[CH:13]=3)[C:7]2=[O:8])[CH3:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11378442Potassium cyanateHCID 15451779HCID 15451779, compound

Product 1

HCID 15451778HCID 15451778, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.3 g (0.0254 mol) of N-1-(cyclopropyl)ethyl-6-fluoro-5-methylpyridine-2,3-dicarboximide and 4.1 g (0.051 mol) of potassium cyanate were introduced into a mixture of 50 ml of DMF and 1 ml of water at 25° C. with stirring and then stirred at 125° C. for 30 minutes. After concentrating the reaction mixture under reduced pressure, the residue was stirred in succession with methyl tert-butyl ether and with water. Insoluble matter was filtered off with suction, washed with methyl tert-butyl ether and dried under reduced pressure. 3.5 g (56% of theory) of the title compound of m.p. 219°-220° C. were obtained. A further 1.6 g (=26% of theory) of the title compound of m.p. 201°-219° C. were obtained from the organic phase after washing with water and drying over magnesium sulfate (active compound Example 1.059).

Workup

  1. stirringstirred at 125° C. for 30 minutes
  2. concentrationAfter concentrating the reaction mixture under reduced pressure
  3. stirringthe residue was stirred in succession with methyl tert-butyl ether and with water
  4. filtrationInsoluble matter was filtered off with suction
  5. washwashed with methyl tert-butyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-097f30137f44401b9aafc3bd0f96a987
Source dataset
uspto-grants-1996_11
Patent number
US05571774

Reaction notes

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