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

HRID 13836

反応式

HRID 13836 の反応式
[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]

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 687150546-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-(isobutylamino)pyridine-3-carbonitrileHCID 178418689HCID 178418689、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4b001e05ab75496f9739f145f583a4bb
出典データセット
uspto-grants-2010_06
特許番号
US07728141B2

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