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

HRID 2217867

반응식

HRID 2217867 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 25517Ammonium Chloride용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8be4569d1ec84e37980886f9c3832abb
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07408065B2

연결된 노트

불러오는 중…