324519-68-8

Basic information

• Product Name: 4-Pentenamide, 5-chloro-N,N-dimethyl-2-(1-methylethyl)-, (2S,4E)-
• Synonyms: 4-Pentenamide, 5-chloro-N,N-dimethyl-2-(1-methylethyl)-, (2S,4E)-;5-Chloro-2-isopropyl-pent-4-enoic acid dimethylamide;(2S,4E)-5-Chloro-N,N-dimethyl-2-(1-methylethyl)-4-pentenamide;Aliskiren inter-4;(E)-(S)-5-chloro-2-isopropyl-pent-4-enoic acid dimethylamide;(S,E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide;5-CHLORO-2-ISOPROPYL-N, N-DIMETHYLPENT-4-ENAMIDE;(E)-5-chloro-2-isopropyl-N,N-diMethylpent-4-enaMide
• CAS NO: 324519-68-8
• Molecular Formula: C₁₀H₁₈ClNO
• Molecular Weight: 203.71
• Product Categories: Drug Intermediates;Aliskiren Intermediate
• Mol File: 324519-68-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 277 ºC
• Flash Point: 121 ºC
• Appearance: /
• Density: 0.999
• Refractive Index: 1.471
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-Pentenamide, 5-chloro-N,N-dimethyl-2-(1-methylethyl)-, (2S,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenamide, 5-chloro-N,N-dimethyl-2-(1-methylethyl)-, (2S,4E)-(324519-68-8)
• EPA Substance Registry System: 4-Pentenamide, 5-chloro-N,N-dimethyl-2-(1-methylethyl)-, (2S,4E)-(324519-68-8)

Safety Data

• Hazardous Substances Data: 324519-68-8(Hazardous Substances Data)

Usage

Uses

(2S,4E)-5-Chloro-2-isopropyl-N,N-dimethylpent-4-enamide is an intermediate in the preparation of orally active renin inhibitor Aliskiren (A536000).

InChI:InChI=1/C10H18ClNO/c1-8(2)9(6-5-7-11)10(13)12(3)4/h5,7-9H,6H2,1-4H3/b7-5+/t9-/m0/s1

Upstream product

• 124-40-3 dimethyl amine 
• 324519-67-7 (S,E)-ethyl 5-chloro-2-isopropylpent-4-enoate 
• 387353-77-7 methyl (S)-(4E)-5-chloro-2-isopropyl-4-pentenoate 
• 72651-95-7 5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 705259-97-8 dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate 
• 51122-91-9 dimethyl isopropylmalonate 
• 475562-17-5 methyl (4E)-5-chloro-2-isopropyl-4-pentenoate 
• 1358791-91-9 5-(3-chloro-allyl)-5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 324519-66-6 (S)-(4E)-5-chloro-2-isopropyl-4-pentenoic acid 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 393108-57-1 (3S,5S)-5-{(1R,3S)-1-bromo-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one 
• 325154-26-5 (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide 
• 173334-57-1 (2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide 
• 324763-47-5 (2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide 
• 325740-70-3 (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one 
• 324763-46-4 (3S,5S)-5-{(1S,3S)-1-azido-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one 
• 393108-57-1 C₂₅H₃₉BrO₅ 
• 1373444-03-1 C₃₀H₄₉N₅O₅ 
• 172900-70-8 (R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol 

Relevant articles and documents

Preparation method of aliskiren intermediate

The invention relates to a preparation method of an important intermediate trans-(2S)-5-chloro-2-isopropyl-N, N-dimethyl-4-pentanamide for synthesizing aliskiren. The method comprises the following steps: by taking trans-(2S)-5-chloro-2-isopropyl-N, N-dimethyl-4-pentanamide as a raw material and dichloromethane as a solvent, reacting trans-(2S)-5-chloro-2-isopropyl-4-pentenoic acid with 2-chloro-4, 6-dimethoxy-1, 3, 5-triazine under the action of an organic alkali, then reacting with dimethylamine hydrochloride, and carrying out acid washing, alkali washing, drying and reduced pressure distillation to obtain the high-purity target intermediate. According to the method, a one-pot method is adopted, and an acyl chloride intermediate is not separated in the process, so that the risk of chiral carbon racemization of trans-(2S)-5-chloro-2-isopropyl-4-pentenoyl chloride in the reaction and high-temperature distillation processes under a high-temperature acidic condition and the decomposition of acyl chloride in the separation process are avoided, and the purity and yield of a target product are improved; and operation is simple and convenient, the same solvent is adopted in the whole synthesis process, a large amount of organic solvent is saved, the production cost is low, the production efficiency is high, and the method is more suitable for industrial production.

PROCESS FOR PREPARING ALISKIREN AND ITS INTERMEDIATES

The present application relates to a process for the preparation of aliskiren and its pharmaceutically acceptable salts. In particular, the present application relates to a process for the preparation of intermediates for aliskiren, and their conversion to aliskiren or its salts.