Benzenemethanamine, N-ethyl-4-methoxy- → 7-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amine

HRID 921622

Reaction equation

HRID 921622 reaction equation
[Br:1][C:2]1[N:10]2[C:5]([C:6](Cl)=[N:7][C:8]([Cl:11])=[N:9]2)=[N:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([CH2:19][NH:20][CH2:21][CH3:22])=[CH:17][CH:16]=1>C1COCC1>[Br:1][C:2]1[N:10]2[C:5]([C:6]([N:20]([CH2:21][CH3:22])[CH2:19][C:18]3[CH:23]=[CH:24][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)=[N:7][C:8]([Cl:11])=[N:9]2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 296018Benzenemethanamine, N-ethyl-4-methoxy-HCID 867084727-Bromo-2,4-dichloroimidazo[2,1-f][1,2,4]triazine

Product 1

HCID 867084717-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amineYield 106.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(I10A): A solution of 7-bromo-2,4-dichloroimidazo[2,1-f][1,2,4]triazine (Intermediate I9F)(10 g, 37.3 mmol) in anhydrous THF (300 ml) was treated with N-(4-methoxybenzyl)ethanamine (8.01 ml, 46.7 mmol), resulting in the immediate precipitation of a solid. The reaction was stirred for 1 hour; the mixture was concentrated in vacuo. To the residue was added EtOAc (100 ml) and the mixture stirred 10 min. The salts were filtered off and the filtrate was washed with 0.5M citric acid, sat. NaHCO3, water and brine. The solution was dried over Na2SO4 and solvents removed to afford 7-bromo-2-chloro-N-ethyl-N-(4-methoxybenzyl)imidazo[2,1-f][1,2,4]triazin-4-amine (15.8 g).

Workup

  1. customresulting in the immediate precipitation of a solid
  2. concentrationthe mixture was concentrated in vacuo
  3. additionTo the residue was added EtOAc (100 ml)
  4. stirringthe mixture stirred 10 min
  5. filtrationThe salts were filtered off
  6. washthe filtrate was washed with 0.5M citric acid, sat. NaHCO3, water and brine
  7. dry with materialThe solution was dried over Na2SO4 and solvents
  8. customremoved

Sources & evidence

ORD record
ord-3df3d869d70f4542ac0f364f2af56bc7
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Linked notes

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