Tetrahydrofuran → tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxo-4-(((pyridin-3-ylmethyl)amino)carbonyl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 39818

Reaktionsgleichung

Reaktionsgleichung von HRID 39818
O1CCCC1.[C:6]([O:10][C:11]([N:13]([CH2:38][C:39]1[CH:48]=[CH:47][C:42]2[O:43][CH2:44][CH2:45][O:46][C:41]=2[CH:40]=1)[CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=3)[C:25]([C:34]([OH:36])=O)=[CH:24][C:23]2=[O:37])[CH2:16][CH2:15]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(Cl)(=O)OCC(C)C.[NH2:57][CH2:58][C:59]1[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=1>O.C(OCC)(=O)C.C(N(CC)CC)C>[O:43]1[C:42]2[CH:47]=[CH:48][C:39]([CH2:38][N:13]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][N:22]4[C:31]5[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=5)[C:25]([C:34]([NH:57][CH2:58][C:59]5[CH:60]=[N:61][CH:62]=[CH:63][CH:64]=5)=[O:36])=[CH:24][C:23]4=[O:37])[CH2:16][CH2:15]3)[C:11](=[O:12])[O:10][C:6]([CH3:8])([CH3:9])[CH3:7])=[CH:40][C:41]=2[O:46][CH2:45][CH2:44]1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 310183-PyridinemethanamineHCID 62365Isobutyl chloroformateHCID 593981451-(2-(4-((Tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

Produkt 1

HCID 59398013tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxo-4-(((pyridin-3-ylmethyl)amino)carbonyl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8471TriethylamineLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To 3.0 mL of tetrahydrofuran suspension containing 0.15 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid, 39 μL of triethylamine was added at room temperature, 36 μL of isobutyl chlorocarbonate was added dropwise under ice-cooling. After the reaction mixture was stirred at the same temperature for 2 hours, 26 μL of 3-(aminomethyl)pyridine was added, further 39 μL of triethylamine was added and stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-90:10], to give 0.12 g of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(7-methoxy-2-oxo-4-(((pyridin-3-ylmethyl)amino)carbonyl)quinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a white foam.

Aufarbeitung

  1. additionwas added at room temperature
  2. temperaturecooling
  3. stirringstirred at the same temperature for 3 hours
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed sequentially with water and aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customThe residue thus obtained
  10. customwas purified by flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-90:10]

Quellen und Nachweise

ORD-Eintrag
ord-afe2231338c5448bb5c115efdf765320
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

Verknüpfte Notizen

Wird geladen…