Water → HCID 178456683, compound

HRID 2044417Notes

Reaction equation

HRID 2044417 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 (1H, m), 7.90 (1H, s), 7.80 (1H, s), 7.47-7.38 (2H, m), 7.26 (1H, s), 5.91 (1H, br, s), 1.59 (6H, 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-4ee9197602c84c828c9f70ca9db5004e
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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