Water → HCID 178456683, compound

HRID 1498257Notes

Reaction equation

HRID 1498257 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 (1H, 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-78c82f4249534f069edc701de36be72c
Source dataset
uspto-grants-2015_12
Patent number
US09198918B2

Reaction notes

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