Nemorexant Chemical Properties

Boiling point:

747.6±70.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMSO : ≥ 250 mg/mL (554.42 mM)

pka

10.47±0.30(Predicted)

InChIKey

NBGABHGMJVIVBW-QHCPKHFHSA-N

SMILES

C(N1CCC[C@]1(C1NC2=C(C)C(Cl)=CC=C2N=1)C)(C1=CC(OC)=CC=C1N1N=CC=N1)=O

Nemorexant Usage And Synthesis

Uses

[(2S)-2-(6-Chloro-7-methyl-1H-benzimidazol-2-yl)-2-methyl-1-pyrrolidinyl][5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone,

Synthesis

Actelion has applied for a patented synthesis of daridorexant. Starting from the raw amino acid 13.1, it was protected by N-Boc with a yield of 80% (Figure 3.4). Next, amide 13.4 was obtained by HATU-mediated amide coupling with o-phenylenediamine 13.3, which was used directly as a crude product in subsequent reactions. Condensation in hot acetic acid gave benzimidazole 13.5 with a yield of 81%. Removal of the N-Boc protecting group with anhydrous dioxane-hydrochloric acid gave pyrrolidine 13.6; however, the salt equivalent and yield of this step were not reported. Carboxylic acid 13.7 was prepared from the corresponding aryl iodide and 1,2,3-triazole by copper-mediated C-N bond coupling, which finally formed an amide bond with pyrrolidine 13.6 to generate daridorexant (13).