Benzyl Bromide → HCID 178491358, compound

HRID 1971453Notes

Reaction equation

HRID 1971453 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:4]=1[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH:15]2[CH2:19][CH2:18][CH2:17][NH:16]2)[N:14]=1)=[NH:8].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1(C2CCCCCCCCC=2)CCCCCCNNN=1>C(#N)C>[CH2:26]([N:16]1[CH2:17][CH2:18][CH2:19][CH:15]1[C:13]1[N:14]=[C:10]([NH:9][C:7]([NH:6][CH2:5][C:4]2[C:3]([O:2][CH3:1])=[CH:23][CH:22]=[CH:21][C:20]=2[O:24][CH3:25])=[NH:8])[S:11][CH:12]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 66692781HCID 66692781, compoundHCID 178491362HCID 178491362, compound

Product 1

HCID 178491358HCID 178491358, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-1f88dd93799246fea6840717908e14e7
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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