Trifluoroacetic acid → 4-[[4-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]aniline

HRID 1674971Notes

Reaction equation

HRID 1674971 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]([F:41])([F:40])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([NH:32]C(=O)OC(C)(C)C)=[CH:28][CH:27]=4)[CH2:21][CH2:20]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1>ClCCl>[F:41][C:9]([F:8])([F:40])[C:10]1[N:14]2[N:15]=[C:16]([N:19]3[CH2:20][CH2:21][N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=4)[CH2:23][CH2:24]3)[CH:17]=[CH:18][C:13]2=[N:12][N:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67339893HCID 67339893, compound

Product 1

HCID 591497504-[[4-[3-(Trifluoromethyl)[1,2,4]triazolo[4,3-b]pyridazin-6-yl]piperazin-1-yl]methyl]anilineYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trifluoroacetic acid (0.5 mL, 0.15 mmol) and tert-butyl 4-((4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazin-1-yl)methyl)phenylcarbamate (0.072 g, 0.15 mmol) in dichloromethane (2 mL) was stirred at ambient temperature for 2 hours and then evaporated to give an involatile residue. The residue was purified by hplc using a Phenomenex Luna C18 100A column (10μ silica, 21 mm diameter, 150 mm length) eluted with decreasingly polar mixtures of water (containing 0.1% TFA) and acetonitrile as eluents to give a partially purified product that was further purified by ion exchange chromatography using an SCX column eluted 7M aquous ammonia in methanol to give 4-((4-(3-(trifluoromethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)piperazin-1-yl)methyl)aniline (0.032 g, 56.2%) as a white solid.

Workup

  1. customevaporated
  2. customto give an involatile residue
  3. customThe residue was purified by hplc
  4. washeluted with decreasingly polar mixtures of water (containing 0.1% TFA) and acetonitrile as eluents
  5. customto give a partially purified product that
  6. customwas further purified by ion exchange chromatography
  7. washeluted 7M aquous ammonia in methanol

Sources & evidence

ORD record
ord-51798283efc547709a865393d41b31d7
Source dataset
uspto-grants-2011_08
Patent number
US08003649B2

Reaction notes

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