1-(4-methoxyphenyl)-N-methylmethanamine → 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-N-(4-methoxybenzyl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine

HRID 1907204

Reaction equation

HRID 1907204 reaction equation
[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:18])[N:11]2[C:16]=1[C:15](Cl)=[N:14][CH:13]=[N:12]2.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][NH:28][CH3:29])=[CH:23][CH:22]=1>ClCCl.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH3:18])[N:11]2[C:16]=1[C:15]([N:28]([CH2:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=1)[CH3:29])=[N:14][CH:13]=[N:12]2

Participants

5

Reactant 2

HCID 4854071-(4-methoxyphenyl)-N-methylmethanamineHCID 866697205-(5-bromo-1-methyl-1H-pyrazol-4-yl)-4-chloro-7-methylimidazo[5,1-f][1,2,4]triazine

Product 1

HCID 681821215-(5-bromo-1-methyl-1H-pyrazol-4-yl)-N-(4-methoxybenzyl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 5-(5-bromo-1-methyl-1H-pyrazol-4-yl)-4-chloro-7-methylimidazo[5,1-f][1,2,4]triazine (9.80 g, 29.9 mmol) in dichloromethane (100 mL) was treated with 1-(4-methoxyphenyl)-N-methylmethanamine (4.52 g, 29.9 mmol). After stirring at room temperature for 10 minutes, the reaction was diluted with saturated aqueous sodium bicarbonate solution (100 mL) and stirred for an additional hour. The organic layer was then washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford the product as a solid. Yield: 12.9 g, 29.2 mmol, 98%. LCMS m/z 443.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.71 (s, 3H), 2.79 (s, 3H), 3.78 (s, 3H), 3.89 (s, 3H), 4.67 (br s, 2H), 6.82 (br d, J=8.7 Hz, 2H), 7.10 (br d, J=8.6 Hz, 2H), 7.64 (s, 1H), 7.92 (s, 1H).

Workup

  1. stirringstirred for an additional hour
  2. washThe organic layer was then washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1129d2a9a864f719a676ae71097a6a2
Source dataset
uspto-grants-2013_12
Patent number
US08598155B2

Linked notes

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