352303-69-6

Basic information

• Product Name: (R)-(2-[5-BROMO-3-(2,6-DIFLUORO-BENZYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDRO-2H-PYRIMIDIN-1-YL]-1-PHENYL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: (R)-(2-[5-BROMO-3-(2,6-DIFLUORO-BENZYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDRO-2H-PYRIMIDIN-1-YL]-1-PHENYL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid,N-[(1R)-2-[5-bromo-3-[(2,6-difluorophenyl)methyl]-3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-1-phenylethyl]-, 1,1-dimethylethyl
• CAS NO: 352303-69-6
• Molecular Formula: C₂₅H₂₆BrF₂N₃O₄
• Molecular Weight: 0
• Mol File: 352303-69-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Density: 1.427g/cm³
• Refractive Index: 1.586
• CAS DataBase Reference: (R)-(2-[5-BROMO-3-(2,6-DIFLUORO-BENZYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDRO-2H-PYRIMIDIN-1-YL]-1-PHENYL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(2-[5-BROMO-3-(2,6-DIFLUORO-BENZYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDRO-2H-PYRIMIDIN-1-YL]-1-PHENYL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(352303-69-6)
• EPA Substance Registry System: (R)-(2-[5-BROMO-3-(2,6-DIFLUORO-BENZYL)-4-METHYL-2,6-DIOXO-3,6-DIHYDRO-2H-PYRIMIDIN-1-YL]-1-PHENYL-ETHYL)-CARBAMIC ACID TERT-BUTYL ESTER(352303-69-6)

Safety Data

• Hazardous Substances Data: 352303-69-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H26BrF2N3O4/c1-15-21(26)22(32)31(24(34)30(15)13-17-18(27)11-8-12-19(17)28)14-20(16-9-6-5-7-10-16)29-23(33)35-25(2,3)4/h5-12,20H,13-14H2,1-4H3,(H,29,33)/t20-/m0/s1

Upstream product

• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 
• 352303-66-3 5-bromo-1-(2,6-difluoro-benzyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 69385-30-4 2,6-difluorobenzylamine 
• 17751-24-5 N-(2,6-difluorobenzyl) urea 
• 352303-65-2 N-1-(2,6-difluorobenzyl)-6-methyluracil 
• 618914-13-9 1-(2,6-difluorobenzyl)-3-(3-oxobutyryl)urea 

Downstream Products

• 352304-04-2 {2-[3-(2,6-difluoro-benzyl)-5-(1-ethoxy-vinyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester 
• 848121-55-1 3-[(2R)-(tert-butoxycarconylamino)-2-phenylethyl]-1-(2,6-difluorobenzyl)-5-(3-methoxyphenyl)-6-methyluracil 
• 352303-90-3 6-Methyl-5-(2-fluorophenyl)-3-[2(R)-tert-butoxycarbonylamino-2-phenylethyl]-1-(2,6-difluorobenzyl)uracil 
• 830346-53-7 3-[2(R)-(tert-butoxycarbonylamino)-2-phenylethyl]-5-(2-fluoro-3-methoxyphenyl)-1-[2,6-difluorobenzyl]-6-methylpyrimidine-2,4(1H,3H)-dione 
• 352290-60-9 [3H]-NBI-42902 

Relevant articles and documents

Gonadotropin Releasing Hormone Receptor Antagonist, Preparation Method Thereof And Pharmaceutical Composition Comprising The Same

Disclosed are compounds useful as gonadotrophin-releasing hormone (“GnRH”) receptor antagonist.

Discovery of sodium R-(+)-4-{2-[5-(2-Fluoro-3-methoxyphenyl)-3-(2-fluoro-6- [trifluoromethyl]-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl] -1-phenylethylamino}butyrate (elagolix), a potent and orally available nonpeptide antagonist of the human gonadotropin-releasing hormone receptor

The discovery of novel uracil phenylethylamines bearing a butyric acid as potent human gonadotropin-releasing hormone receptor (hGnRH-R) antagonists is described. A major focus of this optimization was to improve the CYP3A4 inhibition liability of these uracils while maintaining their GnRH-R potency. R-4-{2-[5-(2-Fluoro-3-methoxyphenyl)-3-(2-fluoro-6-[trifluoromethyl]benzyl) -4-methyl-2,6-dioxo-3,6-dihy-dro-2H-pyrimidin-1-yl]-1-phenylethylamino}butyric acid sodium salt, 10b (elagolix), was identified as a potent and selective hGnRH-R antagonist. Oral administration of 10b suppressed luteinizing hormone in castrated macaques. These efforts led to the identification of 10b as a clinical compound for the treatment of endometriosis.

Synthesis and structure-activity relationships of uracil derived human GnRH receptor antagonists: (R)-3-[2-(2-amino)phenethyl]-1-(2,6-difluorobenzyl)-6- methyluracils containing a substituted thiophene or thiazole at C-5

The design and synthesis of a number of 5-thiazolyl and 5-thienyl substituted uracils is described and results from SAR studies are summarized. The best compound showed Ki = 2 nM. The synthesis of a series of (R)-3-[2-(2-amino)phenethyl]-1-(2,6