1144509-75-0

Usage

Uses

Used in Pharmaceutical Industry:
tert-butyl 2-(5-chlorobenzo[d]oxazol-2-ylaMino)ethylcarbaMate is used as an intermediate in the preparation of Suvorexant, a medication designed to treat insomnia. It is particularly effective in promoting sleep by targeting the orexin receptors in the brain, which are responsible for regulating wakefulness. The compound's unique structure allows it to form stable bonds with other molecules, facilitating the synthesis of Suvorexant and enhancing its therapeutic properties.

Upstream product

• 22876-19-3 5-chloro-2-mercaptobenzoxazole 
• 57260-73-8 N-BOC-1,2-diaminoethane 
• 3621-81-6 2,5-dichloro-1,3-benzoxazole 
• 1251033-26-7 2-bromo-5-chlorobenzo[d]oxazole 
• 17200-29-2 5-chloro-benzoxazole 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 1276666-16-0 C₁₃H₁₆ClN₃O*C₁₈H₁₄O₈ 
• 1276666-14-8 C₁₃H₁₆ClN₃O*C₁₈H₁₄O₈ 

Relevant academic research and scientific papers

A [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] carbamic acid tert-butyl preparation method (by machine translation)

The invention discloses a [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] carbamic acid tert-butyl preparation method, in order to ethylenediamine, vinyl, 2 - amino - 4 - chlorophenol and the like as raw materials, after five-step reaction to obtain the target product [2 - [(5 - chloro - benzo oxazole - 2 - yl) (3 - oxo-butyl) amino] ethyl] tert-butyl carbamate. The invention has simple operation, environment friendly, comprehensive yield is 52% more, than the existing 35.6% yield, with a remarkable enhancement, greatly reduces the production cost of the existing drugs, is suitable for industrial scale production. (by machine translation)

Organocatalytic Visible Light Enabled SNAr of Heterocyclic Thiols: A Metal-Free Approach to 2-Aminobenzoxazoles and 4-Aminoquinazolines

The direct amination reaction of heterocyclic thiols has been developed in the presence of the nonhazardous photocatalyst Rose Bengal under irradiation of visible light. The reaction provides a straightforward approach to pharmaceutically and synthetically useful 2-aminobenzoxazole and 4-aminoquinazoline derivatives from the corresponding heterocyclic thiols with amines in good to excellent yields. Our photochemical reaction can be successfully adapted into a continuous flow reactor which is applicable for large-scale chemical industry. The key benefits of this reaction include the use of metal-free, low-cost Rose Bengal catalyst and practical operation (ambient temperature, open flask, and undried solvents).

A su Wolei lives is an important intermediate for preparing method (by machine translation)

The invention belongs to the field of medical technology, claims an important intermediate {2 - [(5 - chlorobenzene benzene and oxazole -2 yl) - (3 - keto - butyl) - amino] ethyl} - carbamic acid tert-butyl preparation method. The use of the toxicity is relatively small compound in place of the two connecting methyl ketene, the DBU, LDA, NaHMDS, KHMDS catalytic reaction such as, can in order to 90% high yield of the above formula (3) compound, and the HPLC of the crude product content of 99.5% or more, the method of the invention is suitable for industrial production. (by machine translation)

PROCESS FOR THE PREPARATION OF SUVOREXANT AND INTERMEDIATES USEFUL IN THE SYNTHESIS OF SUVOREXANT

A novel processes for the preparation of suvorexant (formula I), its related compounds and its intermediates that are simple, economical and commercially viable. (I)

A method for the synthesis of 2-aminobenzoxazoles

A synthesis of 2-aminobenzoxazoles from the parent C-H compound is described. The procedure involves deprotonation at the 2-position of the benzoxazole and quenching the intermediate organolithium species with a halogen electrophile. The 2-halobenzoxazole is then treated in the same pot with an amine nucleophile to afford the desired product. The substrate scope and selectivity of the reaction are presented. The method is operationally simple and provides access to a variety of amine products bearing additional nucleophilic heteroatoms.

The first large-scale synthesis of MK-4305: A dual orexin receptor antagonist for the treatment of sleep disorder

A new synthetic route to drug candidate 1, a potent and selective dual orexin antagonist for the treatment of sleep disorders, has been developed. The key acyclic precursor 10 was prepared in a one-step process in 75% isolated yield from commercially available starting materials using novel chemistry to synthesize 2-substituted benzoxazoles. A reductive amination was followed by a classical resolution to afford chiral diazepane (R)-11. Finally, coupling of (R)-11 with acid 5 furnished the desired drug candidate 1.

A mild and efficient one-pot synthesis of 2-aminated benzoxazoles and benzothiazoles

Previous syntheses of the biologically active 2-aminated benzoxazoles have relied on forcing thermal conditions to generate the products directly from the corresponding thiols. The resulting yields have ranged from moderate to poor. A mild and high-yielding alternative one-pot chlorination-amination procedure is described. Compounds with a variety of substitution patterns are reported and the methodology has been successfully extended to benzothiazoles. Palladium catalysis on suitably activated examples has been employed to generate the desired compounds of interest.