2-Aminoethanesulphonamide monohydrochloride → 7-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid (2-sulfamoyl-ethyl)-amide

HRID 919807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919807
CO[C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4].Cl.[NH2:25][CH2:26][CH2:27][S:28]([NH2:31])(=[O:30])=[O:29].C[O-].[Na+]>CCO>[S:28]([CH2:27][CH2:26][NH:25][C:3]([C:5]1[N:6]=[CH:7][C:8]2[C:9](=[O:23])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[C:14]=1[OH:15])=[O:4])(=[O:30])(=[O:29])[NH2:31]

Komponenten

5

Edukt 3

HCID 30215492-Aminoethanesulphonamide monohydrochlorideHCID 10942334Sodium MethoxideHCID 682977357-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester

Produkt 1

HCID 601512647-Benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid (2-sulfamoyl-ethyl)-amideAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 7-benzyl-4-hydroxy-8-oxo-7,8-dihydro-[2,7]naphthyridine-3-carboxylic acid methyl ester (30 mg, 0.097 mmol), 2-amino-ethanesulfonic acid amide HCl salt (24 mg, 0.19 mmol), and NaOMe (9.9 mg, 0.18 mmol) in EtOH (2 mL) was heated at 140° C. for 6 h in a microwave reactor. Solvent was evaporated in vacuo, and the residue was partitioned between 1 M HCl and EtOAc. The aqueous layer was extracted with additional EtOAc, and the organic layers were combined and dried over MgSO4. After evaporating the solvent, the crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2) to give 21 mg of the title compound. MS: (+) m/z 403.25 (M+1).

Aufarbeitung

  1. customSolvent was evaporated in vacuo
  2. customthe residue was partitioned between 1 M HCl and EtOAc
  3. extractionThe aqueous layer was extracted with additional EtOAc
  4. dry with materialdried over MgSO4
  5. customAfter evaporating the solvent
  6. customthe crude product was purified by silica gel chromatography (0-10% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-6fbad10ea39e464e81273e5eb5ee1ecc
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

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