138564-58-6

Usage

Uses

An Impurity generated in the preparation of Olanzapine (O253750).

InChI:InChI=1/C5H6N2O2S/c1-3-2-4(7(8)9)5(6)10-3/h2H,6H2,1H3

Upstream product

• 123-38-6 propionaldehyde 
• 4341-85-9 malonitrile 
• 109-77-3 malononitrile 

Downstream Products

• 138564-59-7 2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile 
• 132539-06-1 zyprexa 
• 660861-93-8 2-(4-chloro-2-nitrophenylamino)-5-methylthiophene-3-carbonitrile 
• 660862-12-4 2-(5-fluoro-2-nitrophenylamino)-5-methylthiophene-3-carbonitrile 
• 51486-03-4 2-amino-5-methylthiophene-3-carboxamide 
• 1312592-84-9 3-chloro-N-(2,6-dimethyl-3-phenylthieno[2,3-b]pyridin-4-yl)benzenesulfonamide 
• 1312593-41-1 N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide 
• 1312592-85-0 3-chloro-N-{3-[3-(dimethylamino)phenyl]-2,6-dimethylthieno[2,3-b]pyridin-4-yl}benzenesulfonamide 
• 1312592-94-1 3-chloro-N-[2,6-dimethyl-3-(3-pyridinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312592-97-4 3-chloro-N-[3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-40-0 3-chloro-N-[2,6-dimethyl-3-(phenylmethyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-43-3 3-chloro-N-[2,6-dimethyl-3-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-44-4 3-chloro-N-[2,6-dimethyl-3-(5-methyl-2-furanyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-45-5 3-chloro-N-[2,6-dimethyl-3-(5-methyl-2-thienyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 

Relevant academic research and scientific papers

Easy single-step preparation of ZnO nano-particles by sedimentation method and studying their catalytic performance in the synthesis of 2-aminothiophenes via Gewald reaction

Zinc oxide is a multi-purpose active material with important catalytic applications. In this study, nano-sized ZnO particles were easily synthesized through sedimentation of zinc acetate di-hydrate in absolute ethanol and were characterized by XRD and SEM. The XRD results indicated pure wurtzite structure with the average particle size of 26.9 nm for the nano-particles. It was observed that size of ZnO nano-particles was decreased while solution concentration was increased. This observation would be explained considering enhancing nucleation processes of nano-particles at high concentration of zinc acetate. The prepared nano-particles (2.5 mol%) were used as catalyst for the fast and efficient synthesis of 2-aminothiophenes under solvent free conditions. The three-component mixture of a carbonyl compound, malonodinitrile, and elemental sulfur was converted into the corresponding 2-aminothiophene in moderate to high yields with excellent selectivity.

Ethylene diamine grafted nanoporous UiO-66 as an efficient basic catalyst in the multi-component synthesis of 2-aminithiophenes

This study demonstrates ED-UiO-66 as a novel and effective solid nanoporous basic catalyst prepared through the amine grafting onto the pores of UiO-66. The manufactured nanoparticles were identified by FT-IR, XRD, TGA, FESEM, TEM, CHN and BET and the characterization results certified formation of a single phase nanoporous substance with the medium grain size less than 90?nm. The synthesized material was employed as an efficient catalyst for the preparation of 2-aminotiophenes through the Gewald method. This thermochemically stable nanocatalyst was environmentally safe, reusable and economic. Therefore, this methodology can be simply extended for industrial goals.

Conformational Color Polymorphism and Control of crystallization of 5-Methyl-2-[(4-methyl-2-nitrophenyl)amino]-3-thiophenecarbonitrile

5-Methyl-2-[(4-methyl-2-nitrophenyl)amino]-3-thiophenecarbonitrile is an example of conformational and color polymorphism. The compound crystallizes in red (R), dark red (DR), light red (LR), and orange (O) modifications. There are two specific goals for this study. One is to characterize the complex thermodynamic relationship among these four known forms, and the other is to use the knowledge of the thermodynamic relationship to control the crystallization of these forms. The different forms were characterized by X-ray powder diffractometry as well as Fourier-transform infrared (FT-IR) and Raman spectroscopy; their complex thermodynamic relationships were determined by thermal analysis, solubility measurements, and slurry conversion studies. According to the solubility results, all forms are enantiotropically related: R is the thermodynamically most stable form above 60 deg C, O is the most stable form between room temperature and 60 deg C, LR is the most stable form below - 15 deg C, and DR is metastable throughout the entire temperature range. DR, LR, and O have very similar free energy at ambient temperature, which is the reason for the complex transition behavior. Finally, a schematic energy - temperature diagram was constructed that combines all experimental data in a comprehensive thermodynamic picture and provides insights into how to control the crystallization of the individual forms.

TiO2/nanoclinoptilolite as an efficient nanocatalyst in the synthesis of substituted 2-aminothiophenes

TiO2/nanoclinoptilolite (TiO2/NCP) was prepared by the mediation of hexadecyltrimethylammonium (HDTMA) as surfactant and used as an effective heterogeneous nanocatalyst for the preparation of substituted 2-aminotiophenes. The modified HDTMA/NCP was impregnated with titanium(IV) chloride solution followed by calcination at 500?°C for 20?h. The obtained nanocomposite was characterized using Fourier transform infrared spectroscopy, field emission scanning electron microscopy, inductively coupled plasma optical emission spectroscopy and X-ray diffraction. Moreover, the prepared nanocomposite had high stability and recoverability under mild and solvent-free conditions.

Facile pathway for synthesis of two efficient catalysts for preparation of 2-aminothiophenes and tetrahydrobenzo[b]pyrans

Abstract: We report here a new magnetically recyclable catalyst consisting of iron-substituted Keggin-type heteropolyacid (HPA) grafted on modified Fe3O4 nanoparticles. The synthesized hybrid nanomaterial exhibited the excellent catalytic efficiency in condensation reaction for the preparation of tetrahydrobenzo[b]pyrans under solvent-free conditions as well as in the synthesis of 2-aminothiophenes via Gewald reaction. It must be noted that, HPA supported magnetite nanoparticles catalyzed the preparation of tetrahydrobenzo[b]pyrans, whereas for Gewald reaction amine-functionalized magnetite nanoparticles acted as a catalyst. Different characterization techniques such as Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), field emission scanning electron microscopy (FESEM), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) were used to characterize the hybrid nanomaterial. The reusability of catalyst was affirmed by using in consecutive runs for five times. Performance of prepared catalyst was compared with the various previously reported catalysts; the newly synthesized catalysts found to be most efficient with regard to reaction time, yield and ease of catalyst separation. Graphical Abstract: [Figure not available: see fulltext.].

A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents

Abstract: The synergic effect of choline chloride/urea as a deep eutectic solvent was investigated in the synthesis of 2-aminothiophene derivatives via a three-component cyclocondensation of a ketone or an aldehyde with activated nitriles and elemental sulfur catalyzed by NaOH as cheap and highly accessible base. The advantages of this catalytic protocol are eco-friendly, easy to set up, reusability, and a simple separation and purification of products without using chromatography in high yields at short times. Graphical abstract: [Figure not available: see fulltext.]

[11C]Olanzapine, radiosynthesis and lipophilicity of a new potential PET 5-HT2 and D2 receptor radioligand

Olanzapine and its precursor desmethyl-Olanzapine were synthesized from malononitrile, propionaldehyde, 1-fluoro-2-nitrobenzene, and substituted piperazine in 4, 4, 5, and 5 steps with 35%, 32%, 26%, and 32% overall chemical yield, respectively. [11C]Olanzapine was prepared from desmethyl-Olanzapine with [11C]CH3OTf through N-[ 11C]methylation and isolated by HPLC combined with solid-phase extraction (SPE) in 40-50% radiochemical yield based on [11C]CO 2 and decay corrected to end of bombardment (EOB), with 370-740 GBq/μmol specific activity at EOB. The calculated Log P (C Log P) value of [11C]Olanzapine is 3.39.

A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction

A simple and efficient procedure was developed for the synthesis of multisubstituted 2-aminothiophene derivatives. In the presence of catalytic amount of imidazole, ketones or aldehydes, dicyanomethane and elemental sulfur were converted into the corresponding 2-aminothiophene derivatives in moderate to high yields in DMF at 60 °C.

Process For Producing Pure And Stable Form Of 2-Methyl-4-(4-Methyl-1-Piperazinyl) -10H-Thieno[2,3-B] [1,5] Benzodiazepine

Disclosed is an improved process for producing pure and thermally color stable crystalline Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine and product thereof. The process comprises of reacting 2-(2-aminoanilino)-5-methylthiophene-3-carbonitrile with N-methyl piperazine in conjunction with N-methylpiperazine acid salt, to produce 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine. Also disclosed is a process for obtaining the Polymorphic Form I of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][l,5J benzodiazepine by crystallizing the crude 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine in a mixture of solvents. Further the invention also provides a new polymorph of Olanzapine, dihydrate Form Ji and process for its preparation and a new hydrate Form J2 of Olanzapine having moisture content 1-3% and process for its preparation.

THIENOBENZODIAZEPINE MODULATORS OF D1 RECEPTOR, D2 RECEPTOR, AND/OR 5-HT2 RECEPTOR

The present invention relates to new thienobenzodiazepine modulators of D1 receptors, D2 receptors, and/or 5-HT2 receptors, pharmaceutical compositions thereof, and methods of use thereof.