Piconol → 2-Amino-6-methoxymethyl-N-(6-(pyridin-2-ylmethoxy)-benzofuran-2-ylmethyl)-nicotinamide

HRID 1171206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171206
[NH2:1][C:2]1[N:21]=[C:20]([CH2:22][O:23][CH3:24])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5].O[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[NH2:1][C:2]1[N:21]=[C:20]([CH2:22][O:23][CH3:24])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[O:9][C:10]2[CH:16]=[C:15]([O:17][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:14]=[CH:13][C:11]=2[CH:12]=1)=[O:5]

Komponenten

6

Edukt 4

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 576081922-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide2×

Produkt 1

HCID 576082702-Amino-6-methoxymethyl-N-(6-(pyridin-2-ylmethoxy)-benzofuran-2-ylmethyl)-nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a tetrahydrofuran (2 mL) solution of 2-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide (20 mg, 61 μmol) described in Production Example 5-1 were added 2-(hydroxymethyl)pyridine (6.5 μL, 67 μmol), triphenylphosphine (19.2 mg, 73 μmol) and diethylazodicarboxylate (33 μL, 73 μmol) at room temperature, which was stirred at room temperature for 30 minutes. After filtering the reaction solution, the filtrate was purified by reverse phase high-performance liquid chromatography (using an acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid)) to obtain a mixture of the title compound and 2-amino-N-(6-hydroxy-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide. Then, this mixture was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (6 mg, 24%) as a white solid.

Aufarbeitung

  1. filtrationAfter filtering the reaction solution
  2. customthe filtrate was purified by reverse phase high-performance liquid chromatography (
  3. additionan acetonitrile-aqueous mobile phase (containing 0.1% trifluoroacetic acid))
  4. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-df265b2753744edd813b216b563fe25e
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829585B2

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