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Beclabuvir

Beclabuvir Struktur
958002-33-0
CAS-Nr.
958002-33-0
Englisch Name:
Beclabuvir
Synonyma:
Beclabuvir;Beclabuvir(BMS-791325);(1aR,12bS)-8-cyclohexyl-N-[(dimethylamino)sulfonyl]-1,1a,2,12b-tetrahydro-11-methoxy-1a-[(3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl]-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxamide;Cycloprop[d]indolo[2,1-a][2]benzazepine-9-carboxamide, 12-cyclohexyl-N-[(dimethylamino)sulfonyl]-4b,5,5a,6-tetrahydro-3-methoxy-5a-[(3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl]-, (4bS,5aR)-
CBNumber:
CB12717749
Summenformel:
C36H45N5O5S
Molgewicht:
659.84
MOL-Datei:
958002-33-0.mol

Beclabuvir Eigenschaften

Dichte
1.45±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
L?slichkeit
DMSO:30.0(Max Conc. mg/mL);45.46(Max Conc. mM)
Aggregatzustand
Solid
pka
4.44±0.40(Predicted)
Farbe
White to off-white

Sicherheit

Beclabuvir Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

Beclabuvir is a non-nucleoside, nonstructural protein 5B (NS5B) polymerase inhibitor approved in Japan as part of a fixed-dose combination product for the treatment of hepatitis C virus (HCV). Upon administration and after intracellular uptake, the drug binds to the allosteric, noncatalytic “Thumb 1” site of NS5B resulting in a decreased rate of viral RNA synthesis and replication.4 Beclabuvir is combined with asunaprevir and declatasvir (both approved in 2014) and was discovered and developed by Bristol-Myers Squibb.

Synthese

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?ˉs 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.
Synthesis_958002-33-0

Beclabuvir Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Beclabuvir Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

Global( 32)Lieferanten
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TargetMol Chemicals Inc.
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InvivoChem
+1-708-310-1919 +1-13798911105
sales@invivochem.cn United States 6391 58
TargetMol Chemicals Inc.

support@targetmol.com United States 38631 58
Wuhan Topule Biopharmaceutical Co., Ltd
+8618327326525
masar@topule.com China 8467 58
Aladdin Scientific
+1-+1(833)-552-7181
sales@aladdinsci.com United States 52924 58
Amadis Chemical Company Limited
571-89925085
sales@amadischem.com China 131957 58
Shanghai Biopharmaleader Co., Ltd. +86 18721201413
sales@biopharmaleader.com China 1720 58
Musechem +1-800-259-7612
info@musechem.com United States 4660 60
Fan De(Beijing) Biotechnology Co., Ltd. 15911056312
liming@bio-fount.com China 9729 58
Hangzhou Synstar pharmaceutical Technology CO.,Ltd 0571-85361029
synstar518@163.com China 1990 58

  • Beclabuvir
  • Beclabuvir(BMS-791325)
  • (1aR,12bS)-8-cyclohexyl-N-[(dimethylamino)sulfonyl]-1,1a,2,12b-tetrahydro-11-methoxy-1a-[(3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl]-cycloprop[d]indolo[2,1-a][2]benzazepine-5-carboxamide
  • Cycloprop[d]indolo[2,1-a][2]benzazepine-9-carboxamide, 12-cyclohexyl-N-[(dimethylamino)sulfonyl]-4b,5,5a,6-tetrahydro-3-methoxy-5a-[(3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl)carbonyl]-, (4bS,5aR)-
  • 958002-33-0
  • C36H45N5O5S
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