147118-39-6

Basic information

• Product Name: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate
• Synonyms: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate;ZD-6 ;(3R,6E)-7-[4-(4-Fluorophenyl)-6-(1-methylethyl)-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl]-3-hydroxy-5-oxo-6-heptenoic acid methyl ester;Methyl 7-[4-(4-FLUOROPHENYL)-6-ISO-PROPYL-2-(N-METHYL-N-METHYLSULFONYLAMINO)PYRIMIDIN-5-YL] -(3R,5R)-DIHYDROXY-(E)-6-HEPTENATE;Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-Methyl-N-Methanesul fonylaMino) pyriMidin-5-y;(R,E)-Methyl 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-MethylMethylsulfonaMido)pyriMidin-5-yl)-3-hydroxy-5-oxohept-6-enoate;Methyl (+)-(3R)-7-[4-(4-fluorophenyl)- 6-isopropyl-2-(N-Methyl-NMethansulphonylaMino) pyriMidin-5-yl]-3-hydroxy-5-oxo- 6(E)-heptenoate;5-Oxorosuvastatin Methyl ester
• CAS NO: 147118-39-6
• Molecular Formula: C₂₃H₂₈FN₃O₆S
• Molecular Weight: 493.55
• EINECS: 1312995-182-4
• Mol File: 147118-39-6.mol

Chemical Properties

• Boiling Point: 701.68 °C at 760 mmHg
• Flash Point: 378.163 °C
• Appearance: /
• Density: 1.311
• Vapor Pressure: 1.15E-20mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.87±0.20(Predicted)
• CAS DataBase Reference: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate(147118-39-6)
• EPA Substance Registry System: Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate(147118-39-6)

Safety Data

• Hazardous Substances Data: 147118-39-6(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
2. Used in Synthesis of Rosuvasatatin:
Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate is used as an intermediate in the synthesis of Rosuvasatatin (calcium salt: R700500), a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor. Methyl(+)-(3-R)-7-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesul
fonylamino) pyrimidin-5-yl]-3-hydroxy-5-oxo-6(E)-heptenoate is effective in decreasing high-sensitivity C-reactive protein (hsCRP) and cholesterol concentrations in the blood, making it a valuable component in the treatment of cardiovascular diseases.
3. Used in Drug Delivery Systems:
The compound may also be utilized in the development of drug delivery systems, where its unique structural features can be exploited to improve the targeting, bioavailability, and therapeutic efficacy of various drugs. This application could be particularly relevant in the fields of cancer therapy and other diseases where precise drug targeting is crucial for effective treatment.

InChI:InChI=1/C23H28FN3O6S/c1-14(2)21-19(11-10-17(28)12-18(29)13-20(30)33-4)22(15-6-8-16(24)9-7-15)26-23(25-21)27(3)34(5,31)32/h6-11,14,18,29H,12-13H2,1-5H3/b11-10+/t18-/m1/s1

Upstream product

• 7664-39-3 hydrogen fluoride 
• 147118-38-5 7-(4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonamido)-pyrimidin-5-yl)-(3R)-3-tert-butyldimethylsiloxy-5-oxo-(E)-6-heptenoic acid methyl ester 
• 131466-61-0 (3R)-3-<(tert-Butyldimethylsilyl)oxy>pentanedioic acid 1-<(R)-mandelic acid> ester 
• 1350364-18-9 C₁₅H₂₈O₇Si 
• 1350364-00-9 hydrogen (3R)-1-methyl 3-[(tert-butyldimethylsilyl)-oxy]pentanedioate cyclohexylamine salt 
• 147118-35-2 methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate 
• 147118-37-4 N-[4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl]-N-methylmethanesulfonamide 
• 109744-49-2 Hydrogen (3R)-1-methyl 3-<(tert-butyldimethylsilyl)oxy>pentanedioate 
• 91424-40-7 3-(tert-butyldimethylsilyloxy)glutaric anhydride 
• 147118-30-7 ethyl 2-(N-methyl-N-methanesulfonylamino)-4-(4-fluorophenyl)-6-isopropyl-pyrimidin-5-carboxylic acid 
• 147118-28-3 ethyl 4-(4-fluorophenyl)-6-isopropyl-2-(methylsulfonyl)pyrimidine-5-carboxylate 
• 147118-36-3 N-[4-(4-fluorophenyl)-5-(hydroxymethyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide 
• 147118-27-2 ethyl 4-(4-fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)-pyrimidine-5-carboxylate 
• 147118-32-9 5-ethoxycarbonyl-6-(4'-fluorophenyl)-4-isopropyl-2-(methylamino)pyrimidine 

Downstream Products

• 1416820-70-6 rosuvastatin 1-naphthalen-1-yl-ethylamine salt 
• 1416820-71-7 rosuvastatin (R)-1-(1-naphthyl)ethylamine 
• 852820-97-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidine-5-yl]-3,5-dihydroxyhept-6-enoic acid isopropylamine 
• 1422619-13-3 7-[4-(4-fluorophenyl)-6-isopropyl-2(N-methyl-N-methanesulfonamido)pyrimidin-5-yl]-(3R)-3-hydroxy-5-carbonyl-6-(E)-heptenoic acid 
• 1197348-98-3 3-methylbutyl (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate 
• 917805-74-4 (3R,5S,6E)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-(propan-2-yl)pyrimidin-5-yl]-3,5-dihydroxyhept-6-enoic acid-2-methylpropan-2-amine 
• 1374771-96-6 rosuvastatin, S-benzylisothiourea salt 
• 287714-41-4 rosuvastatin 
• 147118-40-9 (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid methyl ester 

Relevant articles and documents

Preparation process of rosuvastatin calcium preparation

The invention provides a preparation process of a rosuvastatin calcium preparation, and belongs to the technical field of pharmaceutical preparations. With (3R)-tert-butyldimethylsiloxy-5-oxy-6-triphenylphosphoranylidene methyl caproate and 4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl amino)pyridine-5-formaldehyde as initial raw materials, wittig reaction, deprotection reaction, chiral reduction reaction, hydrolysis reaction and purification are carried out so as to obtain a rosuvastatin calcium crude drug; then the rosuvastatin calcium crude drug is uniformly mixed with a diluent, a disintegrating agent, a stabilizing agent and a lubricant so as to obtain a mixture, and then the mixture is tabletted so as to obtain the rosuvastatin calcium preparation. The preparation process of the rosuvastatin calcium preparation disclosed by the invention has the advantages of simple operation, high yield, low cost and stable quality.

A rosuvastatin calcium impurity preparation method

The invention discloses a preparation method of a rosuvastatin calcium impurity. The target compound is produced from 4-(4-fluorophenyl)-6-isopropyl-2(N-methyl-methanesulfonylamino)pyrimidine-5-yl]-formaldehyde and methyl (3R)-3-t-butyldimethylsiloxy-5-carbonyl-6-(triphenylphosphinevinyl)caproate through a Witting reaction, HF deprotection, alkaline hydrolysis and an acidifying reaction. The method has the characteristics of short synthesis route, simple operation, convenient post-treatment, and high purity and high yield of the product. The method provides certain help for register reporting of rosuvastatin calcium, production middle control and improvement of the quality of rosuvastatin calcium.

Preparing rosuvastatin calcium intermediates

The application provides a preparation method for a rosuvastatin calcium intermediate. The method comprises the following steps: a, condensation reaction: a step of adding a main chain Z8 and a side chain J6 into a mixed solution of toluene and acetonitrile, then adding 4-butylammonium bromide, carrying out heating and pressure-reduced concentration so as to obtain a crude H1 product; b, purification of a condensation product: a step of adding a mixture of n-hexane and petroleum ether, and carrying out heating, cooling, heating, filtering and pressure-reduced distillation so as to obtain a H1 product; c, deprotection reaction: a step of adding the H1 product into acetonitrile, then adding an acid-acetonitrile solution under ice bath, after completion of the reaction, controlling a pH value to 7 to 9, then separating the obtained solution and washing an organic layer, further separating the solution and adding a drying agent into the organic layer, then carrying out filtering and pressure-reduced concentration so as to obtain an oily substance, and adding tetrahydrofuran for crystallization so as to obtain an crude H2 product; and d, purification of a deprotection product: a step of adding acetone and tetrahydrofuran, after dissolving, adding activated carbon, and carrying out stirring, hot filtration, cooling, crystallization, filtering and vacuum drying so as to obtain a final H2 product. By using the preparation method for the rosuvastatin calcium intermediate provided by the invention, yield and purity are high, and cost is low.

PROCESS FOR PREPARING ROSUVASTATIN CALCIUM THROUGH NOVEL AMINE SALT

The present invention provides a process for preparing pure rosuvastatin of formula I, or pharmaceutically acceptable salts thereof through rosuvastatin l-(l-naphthyl)ethyl salt of formula II wherein wavy line (>~w) represent (R), (S) stereochemistry or racemate thereof.

PROCESS FOR THE PREPARATION OF ROSUVASTATIN CALCIUM VIA NOVEL AMINE INTERMEDIATE

The present invention, relates to novel amine salts of rosuvastatin and its process for the preparation. Moreover, the present invention also relates to improved process for the preparation of rosuvastatin calcium, employing novel amine salts as an intermediate.

AN IMPROVED PROCESS FOR THE PREPARATION OF AN INTERMEDIATE OF HMG-COA REDUCTASE INHIBITORS

The present invention relates to an improved process for the preparation of intermediates of HMG-CoA reductase inhibitors of Formulae-IXa or IXb and further conversion to HMG-CoA reductase inhibitors and pharmaceutically acceptable salts thereof.

PREPARATION METHOD OF ROSUVASTATIN CALCIUM AND ITS INTERMEDIATES

.A preparation method of rosuvastatin calcium (Formula 1), which can be used for the production of medicament lowering the levels of LDL-cholesterol and triglycerides in vivo, is provided. Such preparation method is suitable for industrial production. Furthermore, the intermediate crystallines used in the preparation method are provided.

CRYSTALLINE FORM OF(7-[4-(4-FLUOROPHENYL)-6-ISOPROPYL-2-(N- METHYL-N-METHYLSULFONYLAMINO)PYRIMIDIN-5-YL]-(3R,5S)- DIHYDROXY-(E)-6-HEPTENOIC ACID INTERMEDIATE, PROCESS FOR PREPARING THE SAME AND USE THEREOF

Disclosed herein is a crystalline form of methyl 7-[4-(4-flourophenyl)-6- isopropyl-2-(N-methyl-N-methylsulfonylamino)-pyrimidin-5-yl]-(3R)-3-hydroxy-5-oxo- (E)-6-heptenate (rosuvastatin intermediate), process for producing the same and using the same for producing rosuvastatin or pharmaceutically acceptable salts thereof.

ROSUVASTATIN DEHYDROABIETYLAMINE SALT

There is provided a compound, which is dehydroabietylamine salt of rosuvastatin. Also provided are processes for making rosuvastatin calcium that include formation of dehydroabietylamine salt of rosuvastatin.

A PROCESS FOR THE PREPARATION OF ROSUVASTATIN INVOLVING A TEMPO-MEDIATED OXIDATION STEP

The present invention provides a process for the preparation of the rosuvastatin intermediate FPP-CHO and its conversion to rosuvastatin and pharmaceutically acceptable salts thereof.