Anisole → 6-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine

HRID 1925139Notes

Reaction equation

HRID 1925139 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:31])([F:30])[C:12]3[N:17]=[N:16][C:15]([NH:18]CC4C=CC(OC)=CC=4OC)=[CH:14][CH:13]=3)=[N:9][N:10]=2)[CH:7]=1.C1(OC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:31])([F:30])[C:12]3[N:17]=[N:16][C:15]([NH2:18])=[CH:14][CH:13]=3)=[N:9][N:10]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 592332696-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine

Product 1

HCID 592332076-((6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amineYield 96%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)-N-(2,4-dimethoxybenzyl)pyridazin-3-amine (16.5 g, 33.6 mmol) and anisole (5.45 g, 50.4 mmol) in TFA (150 mL) was stirred at 70° C. for 30 min. The reaction was concentrated to dryness via rotary evaporation and the resulting residue was sonicated in a solution of Et2O/NaHCO3 (pH=7). The resulting solid was collected by filtration, rinsed with water and then Et2O, and dried in vacuum over P2O5 to provide the title compound, 6-((6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)difluoromethyl)pyridazin-3-amine 45H (11.0 g, 32.2 mmol, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.14 (d, J=9.35 Hz, 1 H) 7.71 (dd, J=9.85, 1.77 Hz, 1 H) 7.92 (d, J=9.35 Hz, 1 H) 7.92 (d, J=10.20 Hz, 1 H) 8.02 (d, J=10.20, 1 H) 8.74 (s, 1 H). ESI-MS:m/z 340.9 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated to dryness via rotary evaporation
  2. customthe resulting residue was sonicated in a solution of Et2O/NaHCO3 (pH=7)
  3. filtrationThe resulting solid was collected by filtration
  4. washrinsed with water
  5. dry with materialEt2O, and dried in vacuum over P2O5

Sources & evidence

ORD record
ord-a97bb9d375f3446c95062acafd1276cd
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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