Hydrochloric Acid → 2-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-8-((trans)-4-methoxypyrrolidin-3-yloxy)quinoline

HRID 1095710Notes

Reaction equation

HRID 1095710 reaction equation
[CH3:1][O:2][C@H:3]1[C@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][O:31][CH3:32])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][N:5](C(OCC2C=CC3C(=CC=CC=3)C=2)=O)[CH2:4]1.Cl.C1COCC1.C([O-])(O)=O.[Na+]>[Pd].CCO>[CH3:32][O:31][CH2:30][CH2:29][O:28][C:26]1[CH:25]=[CH:24][N:23]2[C:19]([C:16]3[CH:15]=[CH:14][C:13]4[C:18](=[C:9]([O:8][C@H:7]5[C@H:3]([O:2][CH3:1])[CH2:4][NH:5][CH2:6]5)[CH:10]=[CH:11][CH:12]=4)[N:17]=3)=[CH:20][N:21]=[C:22]2[CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 131729512(trans)-Naphthalen-2-ylmethyl 3-methoxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

Product 1

HCID 250944922-(7-(2-Methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-8-((trans)-4-methoxypyrrolidin-3-yloxy)quinolineYield 63.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask was charged with (trans)-naphthalen-2-ylmethyl 3-methoxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (0.054 g, 0.087 mmol), 2 N HCl (0.1 mL), THF (1 mL), EtOH (1 mL), and 10% Degussa type Pd/C (0.0186 g, 0.0175 mmol), and the reaction mixture was placed under a balloon of H2 and stirred for 3 hours. The reaction was neutralized with saturated NaHCO3 and filtered (GF/F paper). The filter cake was washed with CHCl3 and water. The layers were separated, the aqueous phase was washed with chloroform, and the organic phase was dried over Na2SO4, filtered and condensed. The residue was purified by silica gel chromatography to provide 24 mg of the desired product. MS APCI (+) m/z 435.2 (M+1) detected.

Workup

  1. filtrationfiltered (GF/F paper)
  2. washThe filter cake was washed with CHCl3 and water
  3. customThe layers were separated
  4. washthe aqueous phase was washed with chloroform
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customcondensed
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b17ccb9c967940ab874a7ad30eed8ef1
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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