Benzoyl chloride, 3-chloro- → HCID 68304348, compound

HRID 1846646Notes

Reaction equation

HRID 1846646 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](=[O:24])[NH:20][CH:21]3[CH2:23][CH2:22]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](=[O:24])[NH:20][CH:21]3[CH2:22][CH2:23]3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 68304347HCID 68304347, compound

Product 1

HCID 68304348HCID 68304348, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.39 g (0.90 mmol) of (3′-amino-5′-cyclopropylcarbamoyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-acetic acid ethyl ester in acetonitrile (5 mL) is treated with 0.14 mL (1.1 mmol) of 3-chlorobenzoyl chloride. The mixture is stirred overnight and then concentrated under reduced pressure. The residue is taken up into water and extracted with ethyl acetate. The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to provide 0.23 g (52%) of [3′-(3-chloro-benzoylamino)-5′-cyclopropylcarbamoyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a colorless foam.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phase is washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-b58f43e090a548e9b1cfba39b4272768
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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