221176-49-4

Basic information

• Product Name: 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity)
• Synonyms: 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity);LY 301664;Olanzapine Impurity;5,10-Dihydro-2-methyl-4H-thieno[2,3-b][1,5]benzodiazepin-4-one(Olanzapine Impurity);Olanzapine Related CoMpound B;Olanzapine Related Compound B (25 mg) (2-methyl-10H-thieno-[2,3-b][1,5]benzodiazepin-4[5H]-one);5,10-Dihydro-2-Methyl-4H-thieno[2,3-b][1,5]benzodiazepin-4-one;Olanzapine EP IMpurity B
• CAS NO: 221176-49-4
• Molecular Formula: C12H10N2OS
• Molecular Weight: 230.2856
• Product Categories: Chemical Impurities;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 221176-49-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 235-237°C
• Boiling Point: 341.1°C at 760 mmHg
• Flash Point: 160.1°C
• Appearance: /
• Density: 1.292g/cm³
• Vapor Pressure: 8.24E-05mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane (Slightly, Heated), Methanol (Slightly)
• PKA: 12.63±0.20(Predicted)
• BRN: 8262494
• CAS DataBase Reference: 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity)(CAS DataBase Reference)
• NIST Chemistry Reference: 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity)(221176-49-4)
• EPA Substance Registry System: 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity)(221176-49-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 221176-49-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity) is used as a reference material for quality control and analytical purposes in the pharmaceutical industry. It helps in the identification, quantification, and control of impurities in the manufacturing process of Olanzapine, ensuring the purity and safety of the final drug product.
Used in Research and Development:
In the field of research and development, 5,10-Dihydro-2-methyl-4H-thieno[2,3-β][1,5]benzodiazepin-4-one (Olanzapine Impurity) serves as a valuable compound for studying the synthesis, properties, and potential applications of Olanzapine and its related compounds. This can lead to the discovery of new drugs, improved manufacturing processes, and a better understanding of the therapeutic effects of Olanzapine.

InChI:InChI=1/C12H10N2OS/c1-7-6-8-11(15)13-9-4-2-3-5-10(9)14-12(8)16-7/h2-6,14H,1H3,(H,13,15)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 138564-59-7 2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile 
• 873895-41-1 2-[(2-aminophenyl)amino]-5-methylthiophene-3-carbonitrile 
• 138564-60-0 4-amino-2-methyl-10H-thieno[2,3-b][1,5]benzodiazepine hydrochloride 

Downstream Products

• 612507-13-8 2-methyl-4,9-dihydro-3-thia-4,9-diazabenzo[f]azulene-10-thione 

Relevant articles and documents

Reductive Condensation of a Nitro Group with Carboxylic Acids Promoted by Phosphorus(III) Compounds: A Short Route to 5 H -Dibenzo[ b, e ][1,4]diazepin-11(10 H)-ones

Tributyl- or triphenylphosphine promotes a one-pot, three-step method for the synthesis of differently substituted dibenzodiazepinones from N -aryl-2-nitroanilines. Pyridine analogues and the corresponding thiazepinones can also be formed using this method. The process involves deoxygenation of the nitro group, then formation of an iminophosphorane intermediate and its intramolecular condensation with a carboxyl group placed in the N -aryl group. The role of the carboxyl group in the formation of the iminophosphorane and the mode of cyclization are discussed.

Bifunctional solid catalysts for chemoselective hydrogenation-cyclisation- amination cascade reactions of relevance for the synthesis of pharmaceuticals

The benzodiazepines olanzapine and clozapine are nowadays manufactured by a three-step process with a final yield below 50%. An approach to environmentally-friendly intensive processes consists in the development of multifunctional solid catalyst able to catalyze multistep reactions. Here, a bifunctional metal-acid solid catalyst has been prepared and is able to carry out hydrogenation-cyclisation-amination reactions in a cascade process. The catalytic system is illustrated for the synthesis of these important antipsychotics, being an alternative for the current industrial process that requires three steps batch reactions, using mineral acids and bases, and stoichiometric amounts of SnCl2.

A PROCESS FOR THE PREPARATION OF N-DEMETHYLOLANZAPINE

The invention relates to the process for the preparation of N- demethylolanzapine and the use of N-demethylolanzapine obtained by the process for the preparation of antipsychotic medicament olanzapine. According to the process of the invention the reaction of an- hydrous piperazine with 4-amino-2-methyl-10H-thieno[2.3-b]- [1.5]benzodiazepine or its inorganic acid addition salt is carried out in molten piperazine, in the absence of a solvent.

PIPERAZINE SUBSTITUTED ARYL BENZODIAZEPINES

Described herein are compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, S, and O; Alk is (C1-4) alkylene or hydroxy substituted (C1-4) alkylene; X is oxygen or sulfur; R1 is hydrogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, or -CN; R2 is H, halogen, (C1-6) fluoroalkyl, (C1-6) cycloalkyl, OR4, SR4, N02, CN, COR4, C(O)OR4, CONR5R6 , NR5R6, S02NR5R6, NR5COR4, NR5SO2R4, optionally substituted aromatic, or (C1-6) alkyl, wherein (C1-6) alkyl is unsubstituted or substituted with a hydroxy group; R3 is hydrogen, (C1-6) fluoroalkyl, (C2-6) alkenyl, Ar, (C1-4)alkyl-Ar, or (C1-4) alkyl wherein (C1-4) alkyl is unsubsituted or substituted with a phenyl; R4 is hydrogen, (C1-6 alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R5 and R6 are independently hydrogen, (C1-6) alkyl, or optionally substituted aromatic, R7 is hydrogen, (C1-6) alkyl, (C1-6) fluoroalkyl, or optionally substituted aromatic; R8 and R9 are independently hydrogen, (C1-6) alkyl, or optionally substituted aromatic; Ar is optionally substituted phenyl, napthyl, monocyclic heteroaromatic or bicyclic heteroaromatic; Z1 and Z2 are independently selected from hydrogen, halogen, (C1-6) alkyl, (C1-6) fluoroalkyl, OR7, SR7, NO2, CN, COR7, CONR8R9, NR8R9, and optionally substituted aromatic; and all salts, solvates, optical and geometric isomers, and crystalline forms thereof. Also, described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treament of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).