Urea → HCID 57929908, compound

HRID 1930063Notes

Reaction equation

HRID 1930063 reaction equation
Br[CH:2]([C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[F:12])=O.[NH2:25][C:26]([NH2:28])=[O:27]>CN(C=O)C>[F:12][C:6]1[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:25]=[C:26]([NH2:28])[O:27][C:2]=1[C:13]1[CH:14]=[CH:15][C:16]2[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=2)[N:18]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 579298612-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

Product 1

HCID 57929908HCID 57929908, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (0.500 g, 1.26 mmol, Preparation #A.2) and urea (0.228 g, 3.80 mmol) were added to DMF (5 mL) then heated at about 100° C. for about 2 h. The mixture was cooled to ambient temperature then purified by RP-HPLC (Table 1, Method f). Concentration under reduced pressure of most of the organic solvent resulted in a precipitate which was collected by filtration and dried to give the title compound (0.018 g, 4%): LC/MS (Table 1, Method b) Rt=1.96 min; MS m/z: 357.2 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthen purified by RP-HPLC (Table 1, Method f)
  3. concentrationConcentration under reduced pressure of most of the organic solvent
  4. customresulted in a precipitate which
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-3372cbe3352f449c99ce4337adc83b64
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

Loading…