Hydrochloric Acid → 8-((4-Fluoropiperidin-4-yl)methoxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline

HRID 1095719Notes

Reaction equation

HRID 1095719 reaction equation
[F:1][C:2]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[C:24]([C:27]2[N:31]4[CH:32]=[CH:33][C:34]([O:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:35][C:30]4=[N:29][CH:28]=2)[CH:23]=[CH:22]3)[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.Cl>O1CCOCC1>[F:1][C:2]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][CH:20]=[C:21]3[C:26]=2[N:25]=[C:24]([C:27]2[N:31]4[CH:32]=[CH:33][C:34]([O:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:35][C:30]4=[N:29][CH:28]=2)[CH:23]=[CH:22]3)[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66782159Tert-butyl 4-fluoro-4-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate

Product 1

HCID 250944938-((4-Fluoropiperidin-4-yl)methoxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolineYield 33.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 4-fluoro-4-((2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)methyl)piperidine-1-carboxylate (0.011 g, 0.020 mmol) was dissolved in dioxane (0.5 mL) and treated with 4 M hydrogen chloride in dioxane (0.126 ml, 0.504 mmol). The reaction was stirred at ambient temperature for 24 hours. The mixture was concentrated in vacuo, redissolved and re-concentrated from MeOH three times. The crude material was loaded onto a SiO2 column and eluted with a gradient from 1 to 20% (6% NH4OH in MeOH)/ethyl acetate to provide the desired product (3 mg). 1H NMR (400 MHz, CDCl3) δ 10.67 (d, 1H), 8.22 (s, 1H), 8.08 (d, 1H), 7.83 (s, 1H), 7.41-7.33 (m, 2H), 7/09-6.98 (m, 2H), 6.90-6.84 (m, 1H), 4.29-4.16 (m, 3H), 3.87-3.79 (m, 2H), 3.49 (s, 3H), 3.23-3.10 (m, 3H), 2.29-2.15 (m, 1H), 2.14-1.94 (m, 2H), 0.93-0.81 (m, 1H). MS APCI (+) m/z 451.2 (M+1) detected.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionredissolved
  3. concentrationre-concentrated from MeOH three times
  4. washeluted with a gradient from 1 to 20% (6% NH4OH in MeOH)/ethyl acetate

Sources & evidence

ORD record
ord-127cd1639f254824bc8282c311614a8c
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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