Sodium Bicarbonate → 7-methoxy-1-(2-(4-(((5-methoxy-4-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one

HRID 385674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385674
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][N:11]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([O:21][CH3:22])[CH:19]=3)[CH:14]=[CH:13][C:12]2=[O:23])[CH2:5][CH2:4]1.C[O-].[Na+].CO.[CH3:29][O:30][C:31]1[C:32]([CH3:39])=[CH:33][C:34]([CH:37]=O)=[N:35][CH:36]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>CO.O.C(Cl)(Cl)Cl.C(O)(=O)C>[CH3:22][O:21][C:18]1[CH:19]=[C:20]2[C:15]([CH:14]=[CH:13][C:12](=[O:23])[N:11]2[CH2:10][CH2:9][N:6]2[CH2:5][CH2:4][CH:3]([NH:2][CH2:37][C:34]3[CH:33]=[C:32]([CH3:39])[C:31]([O:30][CH3:29])=[CH:36][N:35]=3)[CH2:8][CH2:7]2)=[N:16][CH:17]=1

Komponenten

10

Edukt 5

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23694274Sodium methanolate methanolHCID 578153485-Methoxy-4-methylpyridine-2-carbaldehydeHCID 689270711-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride

Produkt 1

HCID 578153787-methoxy-1-(2-(4-(((5-methoxy-4-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-oneAusbeute 38,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a suspension of 0.20 g of 1-(2-(4-aminopiperidin-1-yl)ethyl)-7-methoxy-1,5-naphthyridin-2(1H)-one hydrochloride in 2 mL of methanol, 0.28 g of a 28% sodium methoxide/methanol solution, 73 mg of 5-methoxy-4-methylpyridine-2-carbaldehyde and 28 μL of acetic acid were added. Then, 61 mg of sodium cyanoborohydride was added thereto, and the mixture was stirred at room temperature for 1 hour 30 minutes. To the reaction mixture, chloroform, a saturated aqueous sodium hydrogen carbonate solution and water were added. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by basic silica gel column chromatography using gradient elution with chloroform:methanol=93:7 to 86:14 to obtain 82 mg of 7-methoxy-1-(2-(4-(((5-methoxy-4-methylpyridin-2-yl)methyl)amino)piperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one as a light yellow solid.

Aufarbeitung

  1. additionwere added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with chloroform
  4. washthe resultant solution was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by basic silica gel column chromatography
  8. washelution with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-a17909f325d94a829cdaf7947ea5cf6f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367831B2

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