Water → N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-(2-dimethylamino ethylaminomethyl)pyridine-2-carboxylic acid amide

HRID 217634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 217634
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23]OS(C)(=O)=O)=[CH:19][N:18]=2)=[O:16])=[CH:11][S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33].C(OCC)(=O)C.O>ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([NH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][NH:33][CH2:32][CH2:31][N:30]([CH3:34])[CH3:29])=[CH:19][N:18]=2)=[O:16])=[CH:11][S:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 66053N,N-DimethylethylenediamineHCID 86652250N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide

Produkt 1

HCID 67050142N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-(2-dimethylamino ethylaminomethyl)pyridine-2-carboxylic acid amideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(4-t-Butoxycarbonylaminothiophen-3-yl)-5-methanesulfonyloxymethylpyridine-2-carboxylic acid amide (Reference Compound No. 4-1, 0.36 g, 0.83 mmol) and N,N-dimethylethylenediamine (0.46 mL, 4.2 mmol) were dissolved in anhydrous dichloromethane (5.0 mL)-anhydrous acetonitrile (5.0 mL), and then the reaction mixture was stirred at room temperature for 1.5 hours. Ethyl acetate (0.10 L) and water (0.10 L) were added to the reaction solution, and then the mixture was partitioned. The organic layer was washed with brine (0.10 L), dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform-methanol) to give 98 mg of the title reference compound as a brown amorphous product. (Yield 28%)

Aufarbeitung

  1. customthe mixture was partitioned
  2. washThe organic layer was washed with brine (0.10 L)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform-methanol)
  6. customto give 98 mg of the title reference compound as a brown amorphous product

Quellen und Nachweise

ORD-Eintrag
ord-ac18e52bda5d49e2849ba86806d2b12b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198271B2

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