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

HRID 40004

Reaktionsgleichung

Reaktionsgleichung von HRID 40004
O[C:2]1([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)N=[CH:13][C:12]2=[O:23])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[O:24]1[C:33]2[CH:32]=[C:31]([CH2:34][NH2:35])N=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1.[C:36](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:37].[Na+].[C:50](=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[O:27]1[C:28]2[CH:29]=[CH:50][C:31]([CH2:34][NH:35][CH:5]3[CH2:4][CH2:3][CH:2]([CH2:9][CH2:10][N:11]4[C:20]5[C:15](=[CH:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=5)[C:36]([CH3:37])=[CH:13][C:12]4=[O:23])[CH2:7][CH2:6]3)=[CH:32][C:33]=2[O:24][CH2:25][CH2:26]1

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 593979991-(2-(1-hydroxy-4-oxocyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-oneHCID 593981871-(2,3-Dihydro[1,4]dioxino[2,3-c]pyridin-7-yl)methanamine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 4 mL of a dichloromethane solution containing 90 mg of 1-(2-(1-hydroxy-4-oxocyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one, 2 mL of a dichloromethane solution containing 57 mg of 1-(2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-yl)methaneamine and 24 μL of acetic acid were added at room temperature, and stirred at the same temperature for 1.5 hours. To the reaction mixture, 59 mg of sodium triacetoxyborohydride was added, and stirred at room temperature for 1.5 hours. To the reaction mixture, aqueous saturated sodium hydrogen carbonate solution and chloroform were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, 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 basic silica gel column chromatography [eluent; chloroform:methanol=50:1], to give (A) 29 mg as a light red oil and (B)24 mg as a light red oil. To the purified products A and B, a mixture of diethyl ether and hexane was added, respectively, and each resulting solid was filtered to give (A) 28 mg of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-hydroxycyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a light red solid and (B) 21 mg of 1-(2-(4-((2,3-dihydro(1,4)dioxino(2,3-c)pyridin-7-ylmethyl)amino)-1-hydroxycyclohexyl)ethyl)-7-methoxyquinoxalin-2(1H)-one as a light red solid.

Aufarbeitung

  1. additionwere added at room temperature
  2. stirringstirred at room temperature for 1.5 hours
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  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 basic silica gel column chromatography [eluent; chloroform:methanol=50:1]

Quellen und Nachweise

ORD-Eintrag
ord-19a3a24807dd49969a171285d5e2fef2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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