| Identification | Back Directory | [Name]
Nemorexant | [CAS]
1505484-82-1 | [Synonyms]
Nemorexant
Daridorexant
Methanone, [(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]- | [Molecular Formula]
C23H23ClN6O2 | [MOL File]
1505484-82-1.mol | [Molecular Weight]
450.92 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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).
 | [storage]
Store at -20°C |
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