Benzoyl chloride, 3-chloro- → HCID 71238641, compound

HRID 1846658Notes

Reaction equation

HRID 1846658 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:17]([NH2:18])=[CH:16][C:15]([C:19]#[N:20])=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2].[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C(#N)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[C:17]([NH:18][C:26](=[O:27])[C:25]3[CH:29]=[CH:30][CH:31]=[C:23]([Cl:22])[CH:24]=3)=[CH:16][C:15]([C:19]#[N:20])=[CH:14][N:13]=2)[CH2:10][CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 68303889HCID 68303889, compound

Product 1

HCID 71238641HCID 71238641, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.043 g (0.15 mol) of (3′-amino-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (3 mL) is added 0.021 mL (0.16 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred at room temperature for 2 hours then concentrated under reduced pressure. The residue is taken up in a saturated aqueous solution of ammonium chloride and 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 give 0.047 g (73%) of [3′-(3-chloro-benzoylamino)-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a light yellow solid.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-c8505327a13d4bcfa7ead8bf20e3146f
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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