Benzoyl chloride, 3-chloro- → HCID 67342733, compound

HRID 1846663Notes

Reaction equation

HRID 1846663 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([NH2:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].[Cl:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>C(#N)C.CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([NH:17][C:23](=[O:24])[C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([Cl:19])[CH:21]=3)=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 67343145HCID 67343145, compound

Product 1

HCID 67342733HCID 67342733, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.45 g (1.7 mmol) of 3′-amino-5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester in acetonitrile (20 mL) is added 0.23 mL (1.0 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature overnight then concentrated under reduced pressure and the residue is taken up in water and extracted with ethyl acetate. The combined organic phase is washed with a 10% aqueous solution of sodium hydroxide followed by brine then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide, after concentration of the eluent, a yellow oil. The oil is dissolved in methanol and upon standing a solid precipitates from solution. The material is collected by filtration and dried on the filter pad to provide 0.38 g (56%) of 5′-chloro-3′-(3-chloro-benzoylamino)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester as a white solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase is washed with a 10% aqueous solution of sodium hydroxide
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography
  7. customto provide
  8. customprecipitates from solution
  9. filtrationThe material is collected by filtration
  10. customdried on the filter pad

Sources & evidence

ORD record
ord-a1d40759d9f443e099be89afff38dbaf
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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