958002-33-0 Usage
Uses
Used in Pharmaceutical Industry:
BMS 791325 is used as an antiviral drug for the treatment of hepatitis C virus (HCV). It works by binding to the allosteric, noncatalytic "Thumb 1" site of NS5B, resulting in a decreased rate of viral RNA synthesis and replication. It is combined with other antiviral drugs such as asunaprevir and daclatasvir to enhance the treatment efficacy and overcome drug resistance.
Synthesis
The syntheses of asunaprevir and declatasvir were described
in an earlier review article.Condensation of
indole-6-carboxylic acid (1) with cyclohexanone under basic
conditions gave acid 2 in quantitative yield. Hydrogenation of
the double bond in 2 using Pearlman’s catalyst was followed by
esterification to give ester 3 in high yield. Bromination of the
indole at the 2-position was accomplished with pyridinium
tribromide, and this was followed by saponification to provide
acid 4. Treatment of 4 with carbonyldiimidazole (CDI)
followed by N,N- dimethylsulfamide and 1, 8 -
diazabicyclo[5.4.0]undec-7-ene (DBU) gave compound 5 in
74% yield. Suzuki coupling of 5 with commercial boronic acid 6
provided intermediate 7, which converted to hemiaminal 8
upon continued heating in 61% yield. Compound 8 was then
treated with methyl 2-(dimethoxyphosphoryl)acrylate (9) to
affect a tandem conjugate addition and Horner?Wadsworth?
Emmons (HWE) olefination to give ester 10. Alternatively, the
Suzuki coupling reaction of 5 with 6 could be stopped at
intermediate 7, which could be treated with 9 to promote the tandem conjugate addition/HWE to give 10. Corey?-Chaykovsky cyclopropanation of 10 using sodium hydride
and trimethylsulfoxonium iodide followed by chiral separation
provided cyclopropane 11 in good yield and >99% enantiomeric
excess (ee). Saponification of the methyl ester of 11
followed by coupling with 3-methyl-3,8-diazabicyclo[3.2.1]-
octane dihydrochloride (12) gave beclabuvir (I) in high yield.
Check Digit Verification of cas no
The CAS Registry Mumber 958002-33-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,5,8,0,0 and 2 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 958002-33:
(8*9)+(7*5)+(6*8)+(5*0)+(4*0)+(3*2)+(2*3)+(1*3)=170
170 % 10 = 0
So 958002-33-0 is a valid CAS Registry Number.
958002-33-0Relevant academic research and scientific papers
Cyclopropyl Fused Indolobenzazepine HCV NS5B Inhibitors
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Page/Page column 54-55, (2008/06/13)
The invention encompasses compounds of formula I as well as compositions and methods of using the compounds. The compounds have activity against hepatitis C virus (HCV) and are useful in treating those infected with HCV.
