Potassium Bicarbonate → HCID 178432629, compound

HRID 1799872Notes

Reaction equation

HRID 1799872 reaction equation
[Br:1][C:2]1[CH:24]=[CH:23][C:5]2[C:6]3[N:10](CCO[C:4]=2[CH:3]=1)[CH:9]=[C:8]([C:14]1[N:15]([CH:20]([CH3:22])[CH3:21])[N:16]=[C:17]([CH3:19])[N:18]=1)[N:7]=3.Cl.BrC1C=CC(C(N)=N)=C([F:36])C=1.C(=O)([O-])O.[K+].BrCC(C1N(C(C)C)N=C(C)N=1)=O>C1COCC1.O>[Br:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]2[NH:10][CH:9]=[C:8]([C:14]3[N:15]([CH:20]([CH3:22])[CH3:21])[N:16]=[C:17]([CH3:19])[N:18]=3)[N:7]=2)=[C:4]([F:36])[CH:3]=1

Participants

7

Reactant 4

HCID 516893Potassium BicarbonateHCID 534078914-Bromo-2-fluorobenzimidamide hydrochlorideHCID 582043229-Bromo-2-(1-isopropyl-3-methyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepineHCID 582048242-bromo-1-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-one

Product 1

HCID 178432629HCID 178432629, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Alternatively, 8-Bromo-2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene may be prepared whereby a mixture of 4-bromo-2-fluoro-benzamidine hydrochloride (5.67 g, 22.3 mmol), potassium hydrogen carbonate (8.95 g, 89.4 mmol), THF (45 mL) and water (10 mL) was heated to reflux and a solution of 2-bromo-1-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-ethanone (5.5 g, 22.3 mmol) in THF (15 mL) added dropwise. The reaction mixture was heated at reflux for 18 h before removal of volatile solvent in vacuo. The resultant suspension was filtered and the residue triturated in hot diethyl ether to give 5-[2-(4-Bromo-2-fluoro-phenyl)-1H-imidazol-4-yl]-1-isopropyl-3-methyl-1H-[1,2,4]triazole as an off-white solid (6.4 g, 79%). 1H NMR 400 MHz (DMSO-d) δ: 7.97 (1H, t, J=8.30 Hz), 7.81 (1H, s), 7.76 (1H, dd, J=10.68, 1.92 Hz), 7.58 (1H, dd, J=8.42, 1.93 Hz), 5.79 (1H, br, m), 2.26 (3H, s), 1.44 (6H, d, J=6.60 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for 18 h before removal of volatile solvent in vacuo
  5. filtrationThe resultant suspension was filtered
  6. customthe residue triturated in hot diethyl ether

Sources & evidence

ORD record
ord-736de17ca71b43a599f04c5b880211d1
Source dataset
uspto-grants-2013_01
Patent number
US08343955B2

Reaction notes

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