Benzoyl chloride, 3-chloro- → HCID 68304427, compound

HRID 1846648Notes

Reaction equation

HRID 1846648 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl:26][C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31]>C(#N)C>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH:18][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][CH:35]=[C:27]([Cl:26])[CH:28]=3)=[CH:16][C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 68304428HCID 68304428, compound

Product 1

HCID 68304427HCID 68304427, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.10 g (0.29 mmol) of (3′-amino-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (5 mL) is added 0.041 mL (0.32 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure. A saturated aqueous solution of ammonium chloride is added and the mixture is extracted with ethyl acetate. The combined organic phase is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.115 g (81%) of [3′-(3-chloro-benzoylamino)-5′-phenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a colorless foam.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additionA saturated aqueous solution of ammonium chloride is added
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-c4e65f6c957c4f66985a20000acf9a35
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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