Formaldehyde → N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamide

HRID 2080219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080219
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][CH2:9][C:10]2[S:11][C:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)=[O:7])=[CH:4][N:3]=1.C1C=C2C(C=C(NCNCCCC(O)=O)C=C2)=CC=1.C=O.[C:45]([O:48][CH2:49]C)(=O)C>CO>[CH2:15]([C:12]1[S:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([NH:1][CH2:45][O:48][CH3:49])=[N:3][CH:4]=2)=[CH:14][CH:13]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 8857Ethyl Acetate2×HCID 1910612-Naphthylaminomethyl-gamma-aminobutyric acidHCID 231303536-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide

Produkt 1

HCID 23130744N-(5-benzylthiophen-2-ylmethyl)-6-(methoxymethyl-amino)-nicotinamideAusbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 6-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide described in Example A-144 (210 mg, 0.65 mmol) and 5,5-dimethylimidazo phospho-2,4-dione (92 mg, 0.71 mmol) in methanol (15 mL) was added an aqueous solution of 37% formaldehyde (2.5 mL) under reflux in three time, and the solution was stirred for 1 hour. NH silica gel was added to the reaction solution, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate), and the title compound (210 mg, 0.57 mmol, 87.6%) was obtained as a white solid.

Aufarbeitung

  1. temperatureunder reflux in three time
  2. additionNH silica gel was added to the reaction solution
  3. customthe solvent was evaporated in vacuo for adsorption, purification

Quellen und Nachweise

ORD-Eintrag
ord-a07a50c3babf45bda94512c29e6abd41
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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