Trifluoroacetic acid → 3-(1-azetidin-3-ylmethyl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

HRID 655301Notes

Reaction equation

HRID 655301 reaction equation
C(OC([N:8]1[CH2:11][CH:10]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:19]=[N:20][C:21]4[C:26]([CH:27]=3)=[CH:25][C:24]([CH2:28][C:29]3[N:33]5[N:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]5=[N:31][N:30]=3)=[CH:23][CH:22]=4)[CH:15]=[N:14]2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[NH:8]1[CH2:11][CH:10]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:19]=[N:20][C:21]4[C:26]([CH:27]=3)=[CH:25][C:24]([CH2:28][C:29]3[N:33]5[N:34]=[C:35]([CH3:38])[CH:36]=[CH:37][C:32]5=[N:31][N:30]=3)=[CH:23][CH:22]=4)[CH:15]=[N:14]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 593202813-{4-[6-(6-Methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinolin-3-yl]-pyrazol-1-ylmethyl}-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 593202613-(1-azetidin-3-ylmethyl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{4-[6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinolin-3-yl]-pyrazol-1-ylmethyl}-azetidine-1-carboxylic acid tert-butyl ester (189 mg) was added 6 mL of TFA:dichloromethane/1:1 solution. The mixture was allowed to sit for 2 hours. The volatiles were removed by rotary evaporation and then Methanol (6 mL) and MP-carbonate (400 mg, 3.18 mmol/g) were added. The resin was filtered and the volatiles were removed in vacuo to obtain a quantitative yield of 3-(1-azetidin-3-ylmethyl-1H-pyrazol-4-yl)-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline. Analytical data presented in Table 2.

Workup

  1. customThe volatiles were removed by rotary evaporation
  2. additionMethanol (6 mL) and MP-carbonate (400 mg, 3.18 mmol/g) were added
  3. filtrationThe resin was filtered
  4. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-63b7b0540a4843faa8aa88b3d5f3b50d
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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