Water → HCID 178456683, compound

HRID 1629224Notes

Reaction equation

HRID 1629224 reaction equation
Cl.[Br:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[NH:8])=[C:5]([F:12])[CH:4]=1.C(=O)([O-])O.[K+].O.Br[CH2:20][C:21]([C:23]1[N:24]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:26][N:27]=1)=O>C1COCC1>[Br:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[NH:9][CH:20]=[C:21]([C:23]3[N:24]([CH:28]([CH3:30])[CH3:29])[N:25]=[CH:26][N:27]=3)[N:8]=2)=[C:5]([F:12])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 534078914-Bromo-2-fluorobenzimidamide hydrochlorideHCID 582044892-bromo-1-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-one

Product 1

HCID 178456683HCID 178456683, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a rapidly stirred mixture of 4-bromo-2-fluoro-benzamidine hydrochloride (9.84 g, 38.8 mmol), potassium hydrogen carbonate (15.6 g, 154.8 mmol), THF (98 mL) and water (16 mL) at reflux was added a solution of 2-bromo-1-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-ethanone (9.0 g, 38.8 mmol) in THF (19 mL) over 15 min. The resulting mixture was stirred for 18 h at reflux before concentrating in vacuo. The resultant residue was treated with water and the solid formed collected by filtration, washed (water, then 1:1 diethyl ether: cyclohexane then diethyl ether) to give 5-[2-(4-Bromo-2-fluoro-phenyl)-1H-imidazol-4-yl]-1-isopropyl-1H-[1,2,4]triazole as a brown solid (10.1 g, 74%). 1H NMR δ (ppm)(CDCl3): 8.21-8.14 (1 H, m), 7.90 (1 H, s), 7.80 (1 H, s), 7.47-7.38 (2 H, m), 7.26 (1 H, s), 5.91 (1 H, br, s), 1.59 (6 H, d, J=6.63 Hz).

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. concentrationbefore concentrating in vacuo
  4. additionThe resultant residue was treated with water
  5. customthe solid formed
  6. filtrationcollected by filtration
  7. washwashed (water

Sources & evidence

ORD record
ord-da248af23a104f989e9bcdc35eb4c3d8
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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