2,3-Dihydro-1,4-benzodioxin-6-methylamine → 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

HRID 39853

Reaktionsgleichung

Reaktionsgleichung von HRID 39853
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:25])=[CH:8][C:9](=[O:24])[N:10]2[CH2:13][CH2:14][C:15]2(C#N)[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)=[CH:5][CH:4]=1.[O:26]1[CH2:31][CH2:30][O:29][C:28]2[CH:32]=[C:33]([CH2:36][NH2:37])[CH:34]=[CH:35][C:27]1=2.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.C(O)C.ClCCl>[O:26]1[C:27]2[CH:35]=[CH:34][C:33]([CH2:36][NH:37][CH:18]3[CH2:17][CH2:16][CH:15]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[C:7]([CH3:25])=[CH:8][C:9]4=[O:24])[CH2:20][CH2:19]3)=[CH:32][C:28]=2[O:29][CH2:30][CH2:31]1

Komponenten

9

Edukt 4

HCID 871022,3-Dihydro-1,4-benzodioxin-6-methylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 675396281-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile

Produkt 1

HCID 593984071-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)cyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-oneAusbeute 44,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel2×HCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a mixture of 3 mL of ethanol and 3 mL of dichloromethane solution containing 0.18 g of 1-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)-4-oxocyclohexanecarbonitrile, 1 mL of ethanol solution containing 0.13 g of (2,3-dihydrobenzo[b][1,4-]dioxin-6-yl)methylamine, 0.30 g of molecular sieves 3A, and 45 μL of acetic acid were added at room temperature. After stirred at 40° C. for 1.5 hours, the mixture was cooled to the room temperature, 36 mg of sodium cyanoborohydride was added, and stirred at the same temperature for 15 min. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, washed with 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 [hexane:ethyl acetate=4:1], to give (A) 36 mg of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a colorless oil and (B) 0.11 g of 4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)-1-(2-(7-methoxy-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)ethyl)cyclohexanecarbonitrile as a white foam.

Aufarbeitung

  1. additionwere added at room temperature
  2. additionwas added
  3. stirringstirred at the same temperature for 15 min
  4. customthe organic layer was separated
  5. washwashed with aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by flash silica gel column chromatography [hexane:ethyl acetate=4:1]

Quellen und Nachweise

ORD-Eintrag
ord-ad125c172a2441629fd8ab4adf51811e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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