Hydrochloric Acid → 4-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-one

HRID 15076Notes

Reaction equation

HRID 15076 reaction equation
Cl.C1COCC1.[Si]([O:14][C@H:15]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=4)=[CH:31][C:30]3=[O:44])=[CH:25][CH:24]=2)[CH2:16]1)(C(C)(C)C)(C)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:43][C:40]1[CH:41]=[CH:42][C:37]([CH2:36][O:35][C:32]2[CH:33]=[CH:34][N:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][N:17]4[CH2:18][CH2:19][C@H:15]([OH:14])[CH2:16]4)=[CH:28][CH:27]=3)[C:30](=[O:44])[CH:31]=2)=[N:38][CH:39]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 684307211-(4-{2-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl]ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one

Product 1

HCID 589649034-[(5-chloro-2-pyridinyl)methoxy]-1-(4-{2-[(3S)-3-hydroxy-1-pyrrolidinyl]ethoxy}phenyl)-1H-pyridin-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5N aqueous hydrochloric acid (2.4 mL, 12 mmols) was added to THF (2.4 mL) solution of 1-(4-{2-[(3S)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl]ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (264.7 mg, 0.48 mmol), and stirred at room temperature for 2 hours. The reaction liquid was neutralized with 1N aqueous sodium hydroxide, extend with chloroform, washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was recrystallized from mixed solvent of ethyl acetate and heptane, to provide the title compound (199.8 mg, 95%).

Workup

  1. customThe reaction liquid
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was recrystallized
  6. additionfrom mixed solvent of ethyl acetate and heptane

Sources & evidence

ORD record
ord-98a6e45d20c14bf48c3dda323bd78c88
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

Loading…