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Chemical Structure| 524-36-7 Chemical Structure| 524-36-7
Chemical Structure| 524-36-7

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Pyridoxylamine 2HCl is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor.

Synonyms: Pyridoxylamine; Pyridoxylamine(dihydrochloride)

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Product Details of Pyridoxylamine 2HCl

CAS No. :524-36-7
Formula : C8H14Cl2N2O2
M.W : 241.12
SMILES Code : OC1=C(CN)C(CO)=CN=C1C.[H]Cl.[H]Cl
Synonyms :
Pyridoxylamine; Pyridoxylamine(dihydrochloride)
MDL No. :MFCD00012808
InChI Key :HNWCOANXZNKMLR-UHFFFAOYSA-N
Pubchem ID :10664

Safety of Pyridoxylamine 2HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Pyridoxylamine 2HCl

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 524-36-7 ]

[ 524-36-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 524-36-7 ]
  • [ 7075-11-8 ]
  • [ 1421929-65-8 ]
YieldReaction ConditionsOperation in experiment
25% To a solution of 2.02 g of NaHCO3 in 20 mL of water was added 2.41 g of pyndoxamine dihydrochloride with stirring. The resultant clear solution on standing overnight deposited a crystalline precipitate. The precipitate was collected by filtration, washed with water and dried. To a solution of 2.02 g of NaHCO3 in 20 mL of water was added 2.41 g of pyndoxamine dihydrochloride with stirring. The resultant clear solution on standing overnight deposited a crystalline precipitate. The precipitate was collected by filtration, washed with water and dried. To a solution of 1-beta-D-arabmofuranosylcytosine 5'-monophosphate 1 (230 mg, 0.71 mmol) in H2O/'BuOH (1 : 1; 15 ml), pyndoxamine 2 (480 mg, 2.85 mmol, 4 equiv.) was dded and the reaction mixture was heated to reflux. A solution of dicyclohexylcarbodiimide (588 mg, 2.85 mmol, 4 equiv.) in BuOH (11.4 ml, 0.25M) was slowly added and refluxed overnight. The reaction mixture was cooled to room temperature and the solids formed were filtered. Evaporation of the solvents followed by purification by flash column chromatography (CH2Cl2/MeOH 9: 1 to 1 : 1) afforded the desired product 3 (85 mg, 0.179 mmol, 25% yield). 1? NMR (500 MHz, DMSO/ D2O exchange): delta 7.7 (s, 1H), 7.67 (d, J= 7.5 Hz, 1H), 6.03 (d, J= 4 Hz, 1H), 5.78 (d, J= 7 Hz, 1H), 4.47 (s, 2H), 3.99 (m, 3H), 3.93 (m, 1H), (3.86-3.80 (m, 3H), 2.8 (s, 3H).
  • 2
  • [ 524-36-7 ]
  • [ 538-75-0 ]
  • [ 7075-11-8 ]
  • C17H23N5O9P(1-)*C21H35N4O2(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of 2.02 g of NaHCO3 in 20 mL of water was added 2.41 g of pyndoxamine dihydrochloride with stirring. The resultant clear solution on standing overnight deposited a crystalline precipitate. The precipitate was collected by filtration, washed with water and dried. To a solution of 2.02 g of NaHCO3 in 20 mL of water was added 2.41 g of pyndoxamine dihydrochloride with stirring. The resultant clear solution on standing overnight deposited a crystalline precipitate. The precipitate was collected by filtration, washed with water and dried. To a solution of 1-beta-D-arabmofuranosylcytosine 5'-monophosphate 1 (230 mg, 0.71 mmol) in H2O/'BuOH (1 : 1; 15 ml), pyndoxamine 2 (480 mg, 2.85 mmol, 4 equiv.) was dded and the reaction mixture was heated to reflux. A solution of dicyclohexylcarbodiimide (588 mg, 2.85 mmol, 4 equiv.) in BuOH (11.4 ml, 0.25M) was slowly added and refluxed overnight. The reaction mixture was cooled to room temperature and the solids formed were filtered. Evaporation of the solvents followed by purification by flash column chromatography (CH2Cl2/MeOH 9: 1 to 1 : 1) afforded the desired product 3 (85 mg, 0.179 mmol, 25% yield). 1? NMR (500 MHz, DMSO/ D2O exchange): delta 7.7 (s, 1H), 7.67 (d, J= 7.5 Hz, 1H), 6.03 (d, J= 4 Hz, 1H), 5.78 (d, J= 7 Hz, 1H), 4.47 (s, 2H), 3.99 (m, 3H), 3.93 (m, 1H), (3.86-3.80 (m, 3H), 2.8 (s, 3H). In the above reaction conditions when H2O BuOH in the ratio of 1 :5 was used, the product was obtained as the carboxamidinium salt 4. The counter ion was removed to obtain as a free acid is as follows. A glass column was loaded with 5 ml of Dowex 50WX8 (H+ form) and thoroughly washed with DI water (5 CV). 0.2 mmol of carboxamidinium salt was loaded on the column and the column was washed further with water (2 CV). Finally the product was eluted with 2.5%NH4OH solution. The appropriate fractions were evaporated and the product was dried under high vacuum to afford the desired product 3.
 

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