Sodium Bicarbonate → 1-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

HRID 39814

Reaktionsgleichung

Reaktionsgleichung von HRID 39814
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([NH:23][CH3:24])=[O:22])=[CH:13][C:12]2=[O:25])[CH2:5][CH2:4]1.C([BH3-])#N.[Na+].[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[CH3:39])[CH:34]=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.CO>[F:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][C:38]=1[CH3:39])[CH2:34][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]([NH:23][CH3:24])=[O:22])=[CH:13][C:12]2=[O:25])[CH2:5][CH2:4]1

Komponenten

8

Edukt 4

HCID 516892Sodium BicarbonateHCID 27745743-Fluoro-4-methylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 675390731-(2-(4-aminopiperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride

Produkt 1

HCID 593984361-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To 3.0 mL of methanol suspension containing 0.12 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide hydrochloride, 38 mg of sodium cyanoborohydride, 37 μL of 3-fluoro-4-methylbenzaldehyde and 69 μL of acetic acid were added at room temperature and stirred at the same temperature for 3 hours. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added to be adjusted to pH 10, 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 flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30], to give 26 mg of 1-(2-(4-((3-fluoro-4-methylbenzyl)amino)piperidin-1-yl)ethyl)-N-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamide as a white solid.

Aufarbeitung

  1. additionwere added at room temperature
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washwashed 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 flash silica gel column chromatography [gradient elution of chloroform:methanol=100:0-70:30]

Quellen und Nachweise

ORD-Eintrag
ord-a3e767bd9a5347eb9c1a95225a49d6e7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524738B2

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