945999-98-4

Basic information

• Product Name: 5-bromo-2-[2-(2,6-dichloro-4- methyl-phenoxy)-ethoxy]-pyridine
• Synonyms: 5-bromo-2-[2-(2,6-dichloro-4- methyl-phenoxy)-ethoxy]-pyridine
• CAS NO: 945999-98-4
• Molecular Formula: C₁₄H₁₂BrCl₂NO₂
• Molecular Weight: 377
• Mol File: 945999-98-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 455.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.520±0.06 g/cm3(Predicted)
• PKA: 1.24±0.22(Predicted)
• CAS DataBase Reference: 5-bromo-2-[2-(2,6-dichloro-4- methyl-phenoxy)-ethoxy]-pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-bromo-2-[2-(2,6-dichloro-4- methyl-phenoxy)-ethoxy]-pyridine(945999-98-4)
• EPA Substance Registry System: 5-bromo-2-[2-(2,6-dichloro-4- methyl-phenoxy)-ethoxy]-pyridine(945999-98-4)

Safety Data

• Hazardous Substances Data: 945999-98-4(Hazardous Substances Data)

Upstream product

• 2432-12-4 2,6-dichloro-4-methylophenol 
• 106-44-5 p-cresol 
• 96-49-1 [1,3]-dioxolan-2-one 
• 624-28-2 2,5-dibromopyridine 
• 921630-64-0 2-(2,6-dichloro-4-methyl-phenoxy)-ethanol 

Downstream Products

• 946002-36-4 6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-methyl ester 
• 1007392-69-9 MK-1597 
• 1206625-79-7 (3'R,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)benzyl]cyclopropylamide acetate 
• 1265907-54-7 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester 
• 1206625-88-8 6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-1'-(2,2,2-trifluoroacetyl)-1',2',5',6'-tetrahydro-[3,4']bipyridinyl-3'-carboxylic acid ethyl ester 
• 1265907-55-8 (3'S,4'S)-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-ethyl ester 
• 1206625-70-8 C₂₄H₂₅Cl₂F₃N₂O₅ 
• 1265907-56-9 C₂₇H₃₄Cl₂N₂O₆ 
• 1206625-73-1 (3'R,4'S)-3'-{[2-chloro-5-(2-methoxy-ethyl)-benzyl]cyclopropylcarbamoyl}-6-[2-(2,6-dichloro-4-methyl-phenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester 
• 1026786-82-2 (3'R,4'S)-6-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 

Relevant articles and documents

A practical synthesis of renin inhibitor MK-1597 (ACT-178882) via catalytic enantioselective hydrogenation and epimerization of piperidine intermediate

A practical enantioselective synthesis of renin inhibitor MK-1597 (ACT-178882), a potential new treatment for hypertension, is described. The synthetic route provided MK-1597 in nine steps and 29% overall yield from commercially available p-cresol (7). The key features of this sequence include a catalytic asymmetric hydrogenation of a tetrasubstituted ene-ester, a highly efficient epimerization/saponification sequence of 4 which sets both stereocenters of the molecule, and a short synthesis of amine fragment 2.

PROCESS FOR MAKING A RENIN INHIBITOR

A salt of the compound (3'R,4'S)-6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide selected from the group consisting of monoacetate salt and bis-D-tartrate salt. In one embodiment of the invention, the salt is (3',4'S)-6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide monoacetate. In one embodiment of the invention, the salt is (3'R, 4'S)-6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide bis-D-tartrate. The invention also describes a asymmetric synthesis of (3'R, 4'S)-6-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-1',2',3',4',5',6'-hexahydro-[3,4']bipyridinyl-3'-carboxylic acid [2-chloro-5-(2-methoxy-ethyl)-benzyl]-cyclopropyl-amide as a monoacetate salt or as a bis-D-tartrate salt

Primary Amines as Renin Inhibitors

The invention relates to novel primary amine derivatives and the use thereof as active ingredients in the preparation of pharmaceutical compositions. The invention also concerns related aspects including processes for the preparation of the compounds, pharmaceutical compositions containing one or more of those compounds and especially their use as inhibitors of renin.