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

HRID 2217867

Reaction equation

HRID 2217867 reaction equation
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

Participants

5

Reactant 2

HCID 86012996N-(2,6-Dichloro-5-quinolinyl)-cyclohexaneacetamideHCID 178511035HCID 178511035, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 25517Ammonium ChlorideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-8be4569d1ec84e37980886f9c3832abb
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Linked notes

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