Tetrahydrofuran → HCID 58964904, compound

HRID 15073Notes

Reaction equation

HRID 15073 reaction equation
C1COCC1.[Si]([O:13][C@@H:14]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][N:37]=4)=[CH:30][C:29]3=[O:43])=[CH:24][CH:23]=2)[CH2:15]1)(C(C)(C)C)(C)C>C(Cl)(Cl)Cl>[Cl:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][O:34][C:31]2[CH:32]=[CH:33][N:28]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH2:19][N:16]4[CH2:17][CH2:18][C@@H:14]([OH:13])[CH2:15]4)=[CH:27][CH:26]=3)[C:29](=[O:43])[CH:30]=2)=[N:37][CH:38]=1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 684310651-{4-[2-((3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl)ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one

Product 1

HCID 58964904HCID 58964904, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Tetra-n-butylamnunium fluoroide (1.0M THF solution, 0.924 mL, 0.92 mmol) was added to THF (2 mL) solution of 1-{4-[2-((3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-pyrrolidinyl)ethoxy]phenyl}-4-[(5-chloro-2-pyridinyl)methoxy]-1H-pyridin-2-one (257.0 mg, 0.46 mmol), and stirred at room temperature for 3 hours. Chloroform was added to the reaction liquid, which then was washed with saturated brine and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on high performance liquid chromatography (YMC-Pack™ pro C-18, 0.1% THF solution: 0.1% TFA acetonitrile solution=10→95%), and the resulting crude title compound was recrystallized fronm ethyl acetate-heptane mixed solvent to provide the title compound (103.1 mg, 50%).

Workup

  1. washthen was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentrating the solvent under reduced pressure
  4. customthe residue was purified on high performance liquid chromatography (YMC-Pack™ pro C-18, 0.1% THF solution: 0.1% TFA acetonitrile solution=10→95%)
  5. customthe resulting crude title compound was recrystallized fronm ethyl acetate-heptane mixed solvent

Sources & evidence

ORD record
ord-5b3405515b1a43678ed703c39430f2ac
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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