Chloroacetyl chloride → 2-chloro-N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutylacetamide

HRID 13836

Reaction equation

HRID 13836 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:13]=[C:12]([NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([C:19]#[N:20])=[CH:10][C:9]=1[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C[Mg+].[Br-].[Cl:31][CH2:32][C:33](Cl)=[O:34]>C1COCC1.CCOC(C)=O>[Cl:31][CH2:32][C:33]([N:14]([C:12]1[C:11]([C:19]#[N:20])=[CH:10][C:9]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:13]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:34]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 687150546-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrileHCID 178418689HCID 178418689, compound

Product 1

HCID 687183172-chloro-N-(6-(2-chlorophenyl)-5-(4-chlorophenyl)-3-cyanopyridin-2-yl)-N-isobutylacetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of Step A EXAMPLE 27 (300 mg) in THF (5.0 mL) was added MeMgBr (0.92 mL, 1.4 M solution in toluene/THF 3:1) at 0° C. The reaction stirred for 5 minutes before adding chloroacetyl chloride (0.08 mL). The reaction stirred about 7 hours and was diluted with EtOAc, washed with 2 M aqueous HCl and brine. The dried solution (Na2SO4) was concentrated and purified via flash chromatography on silica gel gradient eluted with 0-15% EtOAc in hexane affording the title compound. HPLC/MS: 471.9 (M+1), 473.9 (M+3); Rt=4.32 min.

Workup

  1. stirringThe reaction stirred about 7 hours
  2. washwashed with 2 M aqueous HCl and brine
  3. concentrationThe dried solution (Na2SO4) was concentrated
  4. custompurified via flash chromatography on silica gel gradient
  5. washeluted with 0-15% EtOAc in hexane affording the title compound

Sources & evidence

ORD record
ord-4b001e05ab75496f9739f145f583a4bb
Source dataset
uspto-grants-2010_06
Patent number
US07728141B2

Linked notes

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