1,4-Dioxane → [1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

HRID 2269844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2269844
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)([CH2:13][CH2:14]S(C)(=O)=O)[CH2:9]1)=[O:7].C(N(C(C)C)CC)(C)C.[F:43][C:44]1[CH:67]=[CH:66][C:47]([CH2:48][N:49]2[C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=3[N:51]=[C:50]2[C:58]([CH:60]2[CH2:65][CH2:64][NH:63][CH2:62][CH2:61]2)=[O:59])=[CH:46][CH:45]=1.O1CCOCC1>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:13][CH2:14][N:63]2[CH2:64][CH2:65][CH:60]([C:58]([C:50]3[N:49]([CH2:48][C:47]4[CH:46]=[CH:45][C:44]([F:43])=[CH:67][CH:66]=4)[C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=4[N:51]=3)=[O:59])[CH2:61][CH2:62]2)([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[CH2:9]1)=[O:7]

Komponenten

6

Edukt 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 155428834-(1-(4-fluorobenzyl)-1H-benzimidazole-2-carbonyl)piperidineHCID 155428861-(3,4,5-Trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine

Produkt 1

HCID 10190770[1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-[(4-fluorophenyl)methyl]benzimidazol-2-yl]methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-(3,4-dichloro-phenyl)-3-(2-methanesulfonyl-ethyl)-pyrrolidine (0.50 g, 0.94 mmol), diisopropylethylamine (0.24 g, 1.9 mmol), 4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidine (0.47 g, 1.91 mmol), and dioxane (7 mL). Heat to reflux. After 14 hours, cool and partition the reaction mixture between ethyl acetate and water. Extract the organic layer with a saturated sodium bicarbonate solution and a saturated sodium chloride solution. Dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with 12% methanol/ethyl acetate containing 0.1% a concentrated aqueous ammonia solution to give the title compound: Rf=0.35 (silica gel, 12% methanol/ethyl acetate containing 0.1% concentrated aqueous ammonia solution).

Aufarbeitung

  1. temperatureHeat to reflux
  2. temperaturecool
  3. custompartition the reaction mixture between ethyl acetate and water
  4. extractionExtract the organic layer with a saturated sodium bicarbonate solution
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-2be267d6ab2b47c4a7048df5b92659b2
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06329392B1

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