Phenylpropynal → 7-fluoro-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one

HRID 39961

Reaktionsgleichung

Reaktionsgleichung von HRID 39961
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[N:13]=[CH:12][C:11]2=[O:21])[CH2:4][CH2:3]1.[C:22]1([C:28]#[C:29][CH:30]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[F:20][C:17]1[CH:18]=[C:19]2[C:14]([N:13]=[CH:12][C:11](=[O:21])[N:10]2[CH2:9][CH2:8][N:5]2[CH2:4][CH2:3][CH:2]([NH:1][CH2:30][C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:7][CH2:6]2)=[CH:15][CH:16]=1.[C:22]1([C:28]#[C:29][CH2:30][N:1]([CH2:19][C:14]#[C:15][C:42]2[CH:43]=[CH:4][CH:3]=[CH:2][CH:7]=2)[CH:2]2[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][N:10]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[N:13]=[CH:12][C:11]3=[O:21])[CH2:6][CH2:7]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 4

HCID 75740PhenylpropynalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 593979071-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

Produkt 2

HCID 593980247-fluoro-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-oneHCID 593983021-(2-(4-(bis(3-phenyl-2-propyn-1-yl)amino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To 10 mL of a chloroform solution containing 404 mg of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one and 180 mg of phenylpropargylaldehyde, 80 μL of acetic acid were added, and stirred at room temperature for 1 hour. To the reaction mixture, 474 mg of sodium triacetoxyborohydride was added, and stirred overnight. Aqueous saturated sodium hydrogen carbonate solution was added, the organic layer was separated. The organic layer was 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 silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1], to give 224 mg of 7-fluoro-1-(2-(4-(3-phenyl-2-propyn-1-ylamino)piperidin-1-yl)ethyl)quinoxalin-2(1H)-one as brown solid and 158 mg of 1-(2-(4-(bis(3-phenyl-2-propyn-1-yl)amino)piperidin-1-yl)ethyl)-7-fluoroquinoxalin-2(1H)-one as yellow oil.

Aufarbeitung

  1. additionwere added
  2. stirringstirred overnight
  3. customthe organic layer was separated
  4. washThe organic layer was washed with aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography [Silica Gel; Fuji Silysia Chemical Ltd., Chromatorex-NH, eluent; ethyl acetate:hexane=2:1]

Quellen und Nachweise

ORD-Eintrag
ord-6855a81fa42e46d8b0d74602440f0e22
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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