1148154-91-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine is used as an active pharmaceutical ingredient (API) for the development of novel drugs targeting specific receptors or enzymes in the human body. Its unique structure allows for potential interactions with biological targets, making it a promising candidate for the treatment of various diseases and disorders.
Used in Chemical Research:
In the field of chemical research, (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine can be used as a starting material or intermediate in the synthesis of more complex molecules. Its unique structural features can be exploited to create new compounds with potential applications in various industries, such as materials science, agrochemicals, and environmental science.
Used in Drug Synthesis as an Impurity:
(S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine may also be used as an impurity in the synthesis of other drugs. For example, it could be an impurity in the production of Rotigotine (R700700), a non-ergot dopamine agonist drug used for the treatment of Parkinson's disease. The presence of (S)-5-Methoxy-N-propyl-N-(2-(thiophen-2-yl)ethyl)-1,2,3,4-tetrahydronaphthalen-2-aMine as an impurity may affect the drug's efficacy, safety, or stability, and thus, its control and monitoring are essential during the drug manufacturing process.

Upstream product

• 1232344-40-9 (-)-(S)-5-methoxy-2-[N-2-(2-thienyl)ethylamino]tetraline 
• 802294-64-0 propionic acid 
• 107-08-4 1-iodo-propane 
• 19995-38-1 2-(thien-2-yl)ethyl chloride 
• 101403-24-1 (S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride 
• 26478-16-0 2-(2-Bromoethyl)thiophene 
• 1374308-75-4 C₁₄H₁₉NO 
• 32940-15-1 5-methoxy-2-tetralone 
• 1222074-06-7 2-(thiophen-2-yl)ethyl 2-nitrobenzene-1-sulfonate 
• 4018-91-1 2-Amino-5-methoxy-1,2,3,4-tetrahydronaphthalene 
• 105086-92-8 (S)-5-methoxy-2-amino-1,2,3,4-tetrahydronaphthalene 
• 244239-67-6 (S)-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide 

Downstream Products

• 125572-93-2 rotigotine hydrochloride 
• 99755-59-6 rotigotine 
• 1232344-37-4 (2S)-5-methoxy-N-propyl-N-(2'-(thien-2-yl)ethyl)tetralin-2-amine hydrochloride 

Relevant academic research and scientific papers

Preparation method of rotigotine

The invention relates to the technical field of medicine preparation, and discloses a preparation method of rotigotine, which comprises the following steps: by taking 5-methoxy-2-tetralone as an initial raw material, reacting with R-alpha-methylbenzylamine, performing debenzylation reduction and S-mandelic acid chiral resolution, then reacting with a propionyl chloride reagent to generate an amide compound, and then reducing by a sodium borohydride reagent to obtain the rotigotine; and finally, reacting with 2-(thiophene-2-yl) 2-nitric acid benzene sulfonic acid ethyl ester to obtain the rotigotine. The preparation process route is as follows: the rotigotine is mild in preparation condition, simple and convenient to operate, relatively high in yield of key intermediates, high in optical purity and easy for industrial large-scale production, and has a very good application prospect.

Preparation method for rotigotine

The invention discloses a preparation method for rotigotine. The preparation method includes the following steps: S1. performing an amination reduction reaction on a 5-methoxy-2-tetralone solution, tert-butanesulfinamide, a catalyst, and sodium borohydride to obtain a substance A; S2. performing an alkylation reaction on a solution of the substance A, bromopropane, and a basic catalyst to obtain asubstance B; S3. reacting the substance B with a hydrochloric acid methanol solution to obtain a substance C; S4. performing a reaction on the substance C, 2-(2-bromoethyl)thiophene, potassium carbonate, and N,N-dimethylformamide to obtain a substance D; and S5. reacting acetic acid with hydrogen bromide to obtain the rotigotine. The preparation method is simple in operation, is high in yield, ismild in reaction condition, is green and environmentally friendly, is high in purity of the prepared rotigotine, and is suitable for large-scale industrial production.

luo Ti gastrodia tuber of a kind of preparation method

The invention discloses a preparation method of rotigotine, and belongs to the technical field of medicine synthesis. According to the method, 5-methoxy-2-tetralone is used as a raw material for amination, asymmetric reduction, halogenation and methoxyl group removal four step reaction for synthesis of chiral rotigotine {(-)-(S)-2-(N-propyl-N-(2-(2-thiophene) ethyl] amino]-5-hydroxy-1, 2, 3, 4-tetralin}. According to the method, a simplex stereoscopic structural compound is synthesized by stereo selective chemical reaction, in the asymmetric reduction process, hantzsch ester 1, 4-dihydropyridine (HEH) is used as a reducing agent, and chiral phosphoric acid is used as a catalyst to synthesize an important intermediate (S)-2-(N-n-propyl) amido-5-methoxy tetralin (II) with a simplex stereoscopic structure, the use of a chiral reagent for splitting to obtain the simplex stereoscopic structural compound is avoided, the synthesis procedure is shortened, the yield is improveds, and the method is favorable for industrialized production.

S-5-SUBSTITUENT-N-2'-(THIOPHENE-2-YL)ETHYL-TETRALIN-2-AMINE OR CHIRAL ACID SALTS THEREOF AND USE FOR PREPARING ROTIGOTINE

The chiral compound S-5-substituted-N-2′-(thienyl-2-yl-)ethyl-tetralin-2-amine or its chiral acid salts and preparation method thereof are disclosed, and the method for preparing Rotigotine by using the chiral compound is also disclosed. Racemic 5-substituted-N-2′-(thien-2-yl-)ethyl-tetralin-2-amine (compound 1) is resolved by using a conventional chiral acid to obtain an optically pure chiral acid salt of S-5-substituted-N-2′-(thien-2-yl-)ethyl-tetralin-2-amine, which is then dissociated to obtain S-5-substituted-N-2′-(thien-2-yl-)ethyl-tetralin-2-amine (compound 2). The compound 2 or chiral acid salt thereof is alkylated and deprotected to produce rotigotine (compound 5).

S-5-SUBSTITUENT-N-2'-(THIOPHENE-2-YL)ETHYL-TETRALIN-2-AMINE OR CHIRAL ACID SALTS THEREOF AND USE FOR PREPARING ROTIGOTINE

The chiral compound S-5-substituted-N-2-(thienyl-2-yl-)ethyl-tetralin-2-amine or its chiral acid salts and preparation method thereof are disclosed, and the method for preparing Rotigotine by using the chiral compound is also disclosed. Racemic 5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 1) is resolved by using a conventional chiral acid to obtain an optically pure chiral acid salt of S-5-substituted-N,2'-(thien-2-yl-)ethyl-tetralin-2-amine, which is then dissociated to obtain S-5-substituted-N-2'-(thien-2-yl-)ethyl-tetralin-2-amine (compound 2). The compound 2 or chiral acid salt thereof is alkylated and deprotected to produce rotigotine (compound 5).

PROCESSES FOR PREPARING HIGHLY PURE ROTIGOTINE OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein are convenient, industrially advantageous and environmentally friendly processes for the preparation of (?)-(S)-5-hydroxy-2-[N-n-propyl-N-2-(2-thienyl)ethylamino]tetralin (rotigotine) or a pharmaceutically acceptable salt thereof. Provided further herein is a highly pure rotigotine or a pharmaceutically acceptable salt thereof substantially free of impurities, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure rotigotine or a pharmaceutically acceptable salt thereof substantially free of impurities.

PROCESSES FOR PREPARING HIGHLY PURE ROTIGOTINE OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein are convenient, industrially advantageous and environmentally friendly processes for the preparation of (-)-(S)-5-hydroxy-2-[N-n-propyl-N-2-(2-thienyl)ethylamino] tetralin (rotigotine) or a pharmaceutically acceptable salt thereof. Provided further herein is a highly pure rotigotine or a pharmaceutically acceptable salt thereof substantially free of impurities, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure rotigotine or a pharmaceutically acceptable salt thereof substantially free of impurities.