Hydrochloric Acid → (trans)-4-(2-(7-(2-Methoxvethoxv)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidin-3-ol

HRID 1095708Notes

Reaction equation

HRID 1095708 reaction equation
[OH:1][C@H:2]1[C@H:6]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[C:15]([C:18]2[N:22]4[CH:23]=[CH:24][C:25]([O:27][CH2:28][CH2:29][O:30][CH3:31])=[CH:26][C:21]4=[N:20][CH:19]=2)[CH:14]=[CH:13]3)[CH2:5][N:4](C(OCC2C=CC3C(=CC=CC=3)C=2)=O)[CH2:3]1.CCO.Cl>[Pd].C1COCC1>[CH3:31][O:30][CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][N:22]2[C:18]([C:15]3[CH:14]=[CH:13][C:12]4[C:17](=[C:8]([O:7][C@@H:6]5[CH2:5][NH:4][CH2:3][C@H:2]5[OH:1])[CH:9]=[CH:10][CH:11]=4)[N:16]=3)=[CH:19][N:20]=[C:21]2[CH:26]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 131729511(trans)-Naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate

Product 1

HCID 25098433(trans)-4-(2-(7-(2-Methoxvethoxv)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidin-3-olYield 20.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A 25 mL flask was charged with (trans)-naphthalen-2-ylmethyl 3-hydroxy-4-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-yloxy)pyrrolidine-1-carboxylate (0.100 g, 0.165 mmol), EtOH (1.6 mL), THF (1.6 mL), 2 N HCl (0.2 mL) and 10% Degussa type Pd/C (0.018 g, 0.017 mmol), and the reaction was placed under a balloon of H2 and stirred for 2 hours. The reaction was filtered (GF/F paper), the filter paper was washed with 2 N HCl and THF, the aqueous phase was washed with DCM, neutralized with saturated NaHCO3, and then extracted with DCM. The organic layer was dried and condensed to afford 14 mg of the desired product. MS APCI (+) m/z 421.2 (M+1) detected.

Workup

  1. filtrationThe reaction was filtered (GF/F paper)
  2. washthe filter paper was washed with 2 N HCl and THF
  3. washthe aqueous phase was washed with DCM
  4. extractionextracted with DCM
  5. customThe organic layer was dried
  6. customcondensed

Sources & evidence

ORD record
ord-7caf852f20864c8c885edf583a0ba40a
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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