Ethyl isocyanate → N-(7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N′-ethylurea

HRID 2112928Notes

Reaction equation

HRID 2112928 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([NH2:11])[N:10]=[C:4]2[CH:3]=1.[CH2:12]([N:14]=[C:15]=[O:16])[CH3:13]>C1COCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([NH:11][C:15]([NH:14][CH2:12][CH3:13])=[O:16])[N:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 545940257-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine2×

Product 1

HCID 57643071N-(7-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)-N′-ethylurea

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Conditions

Temperature
100 °C

Procedure

7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (compound 3, 1.22 g, 5.73 mmol) was dissolved in THF/toluene (1:1, 60 mL), then ethyl isocyanate (4.07 g, 57.3 mmol) and a catalytic quantity of dibutyltindiacetate (6 drops) were added to the mixture. The reaction was then heated in a sealed tube at 100° C. for 24 h. This mixture was allowed to cool, then the solvents removed under reduced pressure to afford an oily solid, which was triturated with Et2O, giving a solid which was collected by filtration. Further material was isolated by flash chromatography of the resulting filtrate on silica (2% MeOH/CH2Cl2 as eluant) to give compound 1-(7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-ethyl-urea (4) LCMS (APCI+) 284, 286.

Workup

  1. temperatureto cool
  2. customthe solvents removed under reduced pressure
  3. customto afford an oily solid, which
  4. customwas triturated with Et2O
  5. customgiving a solid which
  6. filtrationwas collected by filtration
  7. customFurther material was isolated by flash chromatography of the resulting filtrate on silica (2% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-a2bf9849ae4f40009ca4f01118b19024
Source dataset
uspto-grants-2009_04
Patent number
US07524860B2

Reaction notes

Loading…