Home Cart Sign in  
Chemical Structure| 56973-26-3 Chemical Structure| 56973-26-3
Chemical Structure| 56973-26-3
Product Citations

Alternative Products

Product Details of Bredinin aglycone

CAS No. :56973-26-3
Formula : C4H5N3O2
M.W : 127.10
SMILES Code : C1=NC(=C([NH]1)C(=O)N)O
Synonyms :
5-Hydroxy-1H-imidazole-4-carboxamide; SM-108
MDL No. :MFCD09753122
InChI Key :UEWSIIBPZOBMBL-UHFFFAOYSA-N
Pubchem ID :124343

Safety of Bredinin aglycone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Bredinin aglycone

* 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.

  • Upstream synthesis route of [ 56973-26-3 ]

[ 56973-26-3 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 66934-73-4 ]
  • [ 56973-26-3 ]
YieldReaction ConditionsOperation in experiment
12.6 g With hydrogenchloride; sodium formate In water at 5 - 50℃; for 2.08333 h; Inert atmosphere Under the nitrogen atmosphere, 20.0 g of 5-hydroxy-1H-imidazole-4-carboxamide hydrochloric acid salt dihydrate prepared according to the method of Reference Example 2 was added to 240 mL of 0.45 mol/L hydrochloric acid and dissolved therein by heating to 50°C. At 50°C, 40 mL aqueous solution containing 14.3 g of sodium formate was added dropwise thereto over 35 minutes. The reaction mixture was cooled and stirred for 90 minutes with the inside temperature of 5°C. The crystal was collected by filtration and then washed with a mixture liquid containing 20 mL of acetone and 40 mL of water followed by 60 mL of acetone to give 12.6 g of 5-hydroxy-1H-imidazole-4-carboxamide·3/4 hydrate as a pale yellow crystal. Water content ratio: 8.6percent (Karl Fischer Method) IR (ATR) 1655, 1619, 1584, 1551 cm-1 [0145] Powder X-ray diffraction pattern is shown in Fig. 8 and Table 3 while the infrared absorption spectrum (ATR method) is shown in Fig. 9.
12.8 g With sodium formate In water at 50℃; Inert atmosphere (2)
Under a nitrogen atmosphere, 5-hydroxy-1H-imidazole-4-carboxamide hydrochloride dihydrate (20.0 g) was added to 0.45 mol/L hydrochloric acid (240 mL), and dissolved therein by heating the mixture to 50° C.
To this solution, a solution of sodium formate (14.3 g) dissolved in water (40 mL) was added dropwise over 33 minutes.
The reaction mixture was cooled to 5° C., and the crystals were collected by filtration, washed with a mixture of acetone (20 mL) and water (40 mL), and then washed with acetone (60 mL) to obtain 5-hydroxy-1H-imidazole-4-carboxamide 3/4 hydrate as pale yellow crystals (12.8 g).
References: [1] Patent: EP2762469, 2014, A1, . Location in patent: Paragraph 0144-0145.
[2] Patent: US2015/51408, 2015, A1, . Location in patent: Paragraph 0039.
  • 2
  • [ 1131657-83-4 ]
  • [ 56973-26-3 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydrogencarbonate In water; acetone Benzene sulfonic acid salt of SM-108 (500 mg; 1.75 mmol) was dissolved into hot water (5 ml). The resulting solution was neutralized with sodium hydrogencarbonate (147 mg; 1.75 mmol) and acetone (40 ml) was added. After stirring, the precipitated colorless crystals were collected by filtration and were dried in vacuo to give SM-108 [2] (218 mg; 1.72 mmol; yield 98percent) as colorless powders
References: [1] Patent: EP2196460, 2010, A1, . Location in patent: Page/Page column 7; 8.
  • 3
  • [ 62009-47-6 ]
  • [ 3473-63-0 ]
  • [ 56973-26-3 ]
References: [1] Patent: EP2196460, 2010, A1, . Location in patent: Page/Page column 6.
  • 4
  • [ 44234-35-7 ]
  • [ 57471-66-6 ]
  • [ 56973-26-3 ]
References: [1] Journal of the American Chemical Society, 1952, vol. 74, # 11, p. 2892 - 2894.
  • 5
  • [ 4342-03-4 ]
  • [ 56973-26-3 ]
References: [1] Journal of Pharmacy and Pharmacology, 1981, vol. 33, # 12, p. 808 - 811.
 

Historical Records

Technical Information

Categories