Water → HCID 58452683, compound

HRID 70719

Reaction equation

HRID 70719 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([C:9]1[CH:14]=[CH:13][C:12]([CH:15](OCC2CCCC2)[C:16]2[N:21]=[C:20]([O:22]C)[C:19]([Cl:24])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].O.[CH:33]1([SH:38])[CH2:37][CH2:36][CH2:35][CH2:34]1>>[C:5]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]([S:38][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:16]2[NH:21][C:20](=[O:22])[C:19]([Cl:24])=[CH:18][CH:17]=2)=[CH:13][CH:14]=1)([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 4

HCID 962WaterHCID 15510CyclopentanethiolHCID 6451240Aluminum(III) ChlorideHCID 673980526-[(4-Tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine

Product 1

HCID 58452683HCID 58452683, compoundYield 25%

Conditions

Temperature
40 °C

Procedure

Aluminum chloride (66 mg) was added to a solution of 6-[(4-tert-butylphenyl)(cyclopentylmethoxy)methyl]-3-chloro-2-methoxypyridine (64 mg) in cyclopentanethiol (1 mL) under ice-cooling, and then the mixture was stirred at 40° C. for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by preparative TLC (hexane:ethyl acetate=1:10) to give the title compound as a pale yellow solid (15 mg, 25%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the solvent was evaporated under reduced pressure
  7. customThe residue was purified by preparative TLC (hexane:ethyl acetate=1:10)

Sources & evidence

ORD record
ord-647e824dcc404ac691cde1adf01144e7
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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