N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamide → N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

HRID 2217867

反応式

HRID 2217867 の反応式
Br[Zn][CH2:3][CH2:4][CH2:5][C:6]#[N:7].Cl[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:29])[C:15]=2[NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:10]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[NH4+]>[Cl:29][C:14]1[C:15]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:3][CH2:4][CH2:5][C:6]#[N:7])[CH:18]=[CH:17]2

参加物

5

反応物 2

HCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamideHCID 178511035HCID 178511035、化合物

生成物 1

HCID 68809609N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 25517Ammonium Chloride溶媒

実験手順

Bromo(3-cyanopropyl)-zinc (30 mL, 0.5 M in tetrahydrofuran) and tetrakis(triphenylphosphine)palladium(0) (86 mg) were added to N-(2,6-dichloro-5-quinolinyl)-cyclohexaneacetamide (Example 1(a)) (500 mg). The reaction mixture was heated to reflux for 30 minutes. The mixture was cooled to room temperature and then poured into aqueous saturated ammonium chloride solution (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried, filtered and evaporated. Purification (SiO2, methanol:dichloromethane 3:97 as eluant) gave the sub-title compound as a solid (490 mg).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customPurification (SiO2, methanol:dichloromethane 3:97 as eluant)

出典と根拠

ORDレコード
ord-8be4569d1ec84e37980886f9c3832abb
出典データセット
uspto-grants-2008_08
特許番号
US07408065B2

関連ノート

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