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ChemicalBook--->CAS DataBase List--->1233855-46-3

1233855-46-3

1233855-46-3 Structure

1233855-46-3 Structure
IdentificationBack Directory
[Name]

BIA10-2474
[CAS]

1233855-46-3
[Synonyms]

CS-2451
BIA10-2474
BIA10-2474; BIA-10-2474
1H-Imidazole-1-carboxamide,N-cyclohexyl-N-methyl-4-(1-oxido-3-pyridinyl)-
[Molecular Formula]

C16H20N4O2
[MDL Number]

MFCD30532661
[MOL File]

1233855-46-3.mol
[Molecular Weight]

300.36
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

DMSO:2.2(Max Conc. mg/mL);7.32(Max Conc. mM)
[form ]

A crystalline solid
[color ]

White to off-white
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Uses]

N-Cyclohexyl-N-methyl-4-(1-oxido-3-pyridinyl)-1H-imidazole-1-carboxamide is a potential fatty acid amide hydrolase (FAAH) inhibitor used for treating and preventing diseases.
[Synthesis]

N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide

1233855-18-9

BIA10-2474

1233855-46-3

In a further step of this synthesis, N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide (90 g, 317 mmol) was dissolved in dichloromethane (1350 ml) in a 2L reactor followed by addition of peracetic acid (84 ml, 475 mmol). The reaction mixture was stirred at 25 °C and the progress of the reaction was monitored by HPLC until N-cyclohexyl-N-methyl-4-(pyridin-3-yl)-1H-imidazole-1-carboxamide was completely consumed. After completion of the reaction, an aqueous solution (270 ml) of sodium metabisulfite (60.2 g, 317 mmol) was slowly added, keeping the reaction temperature below 30 °C. After performing phase separation, the organic phase was washed with water. After phase separation again, the organic phase was concentrated to 1/5 of the original volume at atmospheric pressure.Subsequently, the solvent was replaced with isopropanol (1350 ml) and the suspension was cooled down to 0 °C over a period of 4 hours and stirring was continued at this temperature for 1 hour. The resulting white crystalline solid was collected by filtration and washed sequentially with water (270 ml) and isopropanol (270 ml) to give 84.8 g (89% yield) of the target product.

[in vivo]

In January 2016, severe adverse events (SAE) occurs in the Phase I clinical trial using the drug BIA 10-2474 including one death. The possibilities for failure of trials such as off-target effect, dose calculation, unexpected immune response, species variation, and cumulative dose toxicity would be sought[2].

[storage]

Store at -20°C
[References]

[1] Patent: WO2012/15324, 2012, A1. Location in patent: Page/Page column 58-59
[2] Patent: US2012/65191, 2012, A1. Location in patent: Page/Page column 32
[3] Patent: WO2014/17938, 2014, A2. Location in patent: Page/Page column 67; 68
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