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

HRID 1410812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410812
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-4107b67fc18a402d8a81ffa6c170c453
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921389B2

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