Reaktion #2058635

ord-1f88dd93799246fea6840717908e14e7

Reaktionsgleichung

COc1cccc(OC)c1CNC(=N)Nc1nc(C2CCCN2)cs1
N-(2,6-dimethoxybenzyl)-N′-(4-pyrrolidine-2-yl-1,3-thiazole-2-yl)guanidine
BrCc1ccccc1
benzyl bromide
C1=C(C2=NNNCCCCCC2)CCCCCCCC1
triazabicyclodecene
COc1cccc(OC)c1CNC(=N)Nc1nc(C2CCCN2Cc2ccccc2)cs1
white solid
Ausbeute 50.6%
COc1cccc(OC)c1CNC(=N)Nc1nc(C2CCCN2Cc2ccccc2)cs1
N-[4-(1-benzylpyrrolidine-2-yl)-1,3-thiazole-2-yl]-N′-(2,6-dimethoxybenzyl)guanidine
Ausbeute 50.6%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeChromatography on silica gel (dichloromethane/methanol 0-5%) of the residue obtained
  2. 2
    Sonstigeevaporation concentration

Vorschrift

177 mg N-(2,6-dimethoxybenzyl)-N′-(4-pyrrolidine-2-yl-1,3-thiazole-2-yl)guanidine, Example 147 free base, 100 mg of benzyl bromide and 870 mg polymer-bound triazabicyclodecene (1.3 mmol/g, Argonaut) were shaken in 20 ml acetonitrile overnight at room temperature. Chromatography on silica gel (dichloromethane/methanol 0-5%) of the residue obtained following evaporation concentration yielded 112 mg of a white solid; ESI-MS [M+H+]=452.15.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08431604B2uspto-grants-2013_04