Trifluoroacetic acid → 2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-8-(piperidin-4-yloxy)quinoline

HRID 1095676Notes

Reaction equation

HRID 1095676 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]2[C:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[C:25]([O:32][CH:33]5[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34]5)[CH:26]=[CH:27][CH:28]=4)[N:23]=3)=[CH:20][N:21]=[C:15]2[CH:14]=1>ClCCl>[CH3:8][O:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]2[C:19]([C:22]3[CH:31]=[CH:30][C:29]4[C:24](=[C:25]([O:32][CH:33]5[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]5)[CH:26]=[CH:27][CH:28]=4)[N:23]=3)=[CH:20][N:21]=[C:15]2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66781895Tert-butyl 4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate

Product 1

HCID 250978762-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-8-(piperidin-4-yloxy)quinolineYield 42.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid 0.0862 ml, 1.12 mmol) was added to a solution of tert-butyl 4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)piperidine-1-carboxylate (0.029 g, 0.0559 mmol) in dichloromethane (0.50 mL). After stirring overnight at ambient temperature, the reaction mixture was concentrated under reduced pressure and partitioned between dichloromethane and saturated NaHCO3. The organic layer was washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography (40:1 dichloromethane/MeOH followed by 5:1 dichloromethane/MeOH followed by 2:1 dichloromethane/MeOH) provided 10.0 mg of the desired compound. MS APCI (+) m/z 419.2 (M+1) detected.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompartitioned between dichloromethane and saturated NaHCO3
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified via flash column chromatography (40:1 dichloromethane/MeOH followed by 5:1 dichloromethane/MeOH followed by 2:1 dichloromethane/MeOH)

Sources & evidence

ORD record
ord-140c61ebf95d4a7ea5589f825910a76d
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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