Hydrochloric Acid → N-(2,6-dimethoxybenzyl)-N'-(4-methyl-1,3-oxazole-2-yl)guanidine acetate

HRID 447942Notes

Reaction equation

HRID 447942 reaction equation
[C:1]([NH:3][C:4]([NH:6][CH2:7][C:8]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:9]=1[O:16][CH3:17])=[NH:5])#[N:2].[OH:18][CH2:19][C:20](=O)[CH3:21].Cl>CO.O>[C:13]([OH:14])(=[O:18])[CH3:8].[CH3:17][O:16][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:8]=1[CH2:7][NH:6][C:4]([NH:3][C:1]1[O:18][CH:19]=[C:20]([CH3:21])[N:2]=1)=[NH:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8299HydroxyacetoneHCID 178491370HCID 178491370, compound

Product 1

HCID 178476657N-(2,6-dimethoxybenzyl)-N'-(4-methyl-1,3-oxazole-2-yl)guanidine acetate

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
40 °C

Procedure

0.20 g (0.85 mmol) N-cyano-N′-(2,6-dimethoxybenzyl)guanidine were suspended in 20 ml methanol/water (1:1). Subsequently, 63.3 mg (0.85 mmol) hydroxyacetone were added and the mixture was heated to 40° C. The pH-value was adjusted at high temperature with 1 N HCl to 2.5-3 pH. In total, the reaction mixture was heated for 34 hours at 40° C. under constant pH-control until no further educts could be detected by mass spectrometry. The methanol was distilled off under vacuum and a white solid remained which was purified by HPLC (Merck: Chromolith RP-18E, 100-25; eluent water/acetonitrile/0.1 molar acetic acid); 64 mg.

Workup

  1. temperatureIn total, the reaction mixture was heated for 34 hours at 40° C. under constant pH-control until no further educts
  2. distillationThe methanol was distilled off under vacuum
  3. customwas purified by HPLC (Merck: Chromolith RP-18E, 100-25; eluent water/acetonitrile/0.1 molar acetic acid)

Sources & evidence

ORD record
ord-294008dfdbd64458a077150d033a9819
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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