6397-33-7

Usage

Uses

Used in Pharmaceutical Industry:
2-(isopropylthio)aniline serves as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs due to its unique chemical structure and reactivity.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(isopropylthio)aniline is utilized as a precursor in the production of various agrochemicals, potentially enhancing crop protection and yield through its incorporation into pesticides or other agricultural chemicals.
Used in Dye Industry:
2-(isopropylthio)aniline is also employed as a building block in the creation of dyes, where its specific properties can contribute to the development of novel colorants for various applications, including textiles and other industrial uses.

InChI:InChI=1/C9H13NS/c1-7(2)11-9-6-4-3-5-8(9)10/h3-7H,10H2,1-2H3

Upstream product

• 1551-21-9 methyl isopropyl sulfide 
• 622-37-7 Phenyl azide 
• 75-30-9 2-iodo-propane 
• 137-07-5 2-amino-benzenethiol 
• 75-26-3 isopropyl bromide 
• 70415-85-9 2-(isopropyl sulfanyl)nitrobenzene 
• 1493-27-2 ortho-nitrofluorobenzene 

Downstream Products

• 951695-89-9 N-(2-(isopropylthio)phenyl)-N'-(mesityl)-oxalamide 
• 951695-92-4 N-(2-(isopropylthio)phenyl)-N'-(2,6-diisopropylphenyl)-oxalamide 
• 761440-16-8 2-chloro-N-(2-(isopropylsulfonyl)phenyl)-5-methyl-pyrimidin-4-amine 
• 1609171-11-0 N-(2-(isopropylthio)phenyl)-3-methyl-6-(methylthio)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1609170-60-6 (R)-5-chloro-N-2-(2,5-dimethyl-4-(piperidin-4-yl)-2,3-dihydrobenzofuran-7-yl)-N-4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine 
• 1609170-61-7 (R)-5-chloro-N-2-(2,5-dimethyl-4-(1-methylpiperidin-4-yl)-2,3-dihydrobenzofuran-7-yl)-N-4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine 
• 76697-50-2 1-amino-2-(isopropylsulphonyl)benzene 
• 1032900-25-6 5-chloro-N²-{5-methyl-4-(piperidin-4-yl)-2-[(propan-2-yl)oxy]phenyl}-N⁴-[2-(propane-2-sulfonyl)phenyl]pyrimidine-2,4-diamine 
• 1632485-14-3 2,5-dichloro-N-[2-(propan-2-ylsulfanyl)phenyl]pyrimidin-4-amine 

Relevant academic research and scientific papers

Synthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents

Anaplastic lymphoma kinase (ALK) targeted therapies have demonstrated remarkable efficacy in ALK-positive lung adenocarcinomas. Here we synthesized and evaluated sixteen new 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibitors. The optimal compound 9e exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which is better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the optimal compound 9e decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that 9e could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

The 2-(neopentylsulfinyl)aniline directing group that promotes rapid palladium-catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis-functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1-substituted cyclopropanols were employed as equivalents of vinyl ketones.

The novel anti-tumor medicine synthetic method and a pharmaceutically acceptable salt thereof and solid preparation (by machine translation)

The invention discloses a method for synthesis of antineoplastic agent, the chemical name is 5 - chloro - N2 - (3 - amino-acetyl aminophenyl) - N4 - (2 - [...] phenyl) pyrimidine - 2, 4 - diamine. At the same time, its salt, crystalline form research, select and suitable for further development as a preparation of the maleate, tartrate and succinate and its corresponding crystalline form. The invention also provides a to the antineoplastic agent as the active ingredient of the solid preparation, wherein the supplemented with one or more solubilising. The invention solid preparation dissolution characteristic and excellent stability, with clinical application prospect. (by machine translation)

Preparation method of 2, 5-dichloro-N-(2-(isopropyl sulfonyl)phenyl)pyrimidine-4-amine

The invention relates to a preparation method of 2, 5-dichloro-N-(2-(isopropyl sulfonyl)phenyl)pyrimidine-4-amine. The method has the advantages of simple reaction process, high safety, high yield and mass production capacity.

New intermediate of non-small-cell lung carcinoma treating drug Ceritinib, and preparation method thereof

The present invention relates to the field of pharmaceutical chemistry, to a preparation method of a new intermediate of 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidine-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (Ceritinib). According to the present invention, o-fluoronitrobenzene is adopted as a starting raw material, substitution, reduction and condensation are performed to obtain the new intermediate 2-X-5-chloro-N-(2-(isopropyl sulfide)phenyl)pyrimidine-4-amine (X is halogen, p-methyl benzene sulfonyloxy, methyl sulfonyloxy or trifluoromethylsulfonyloxy), the new intermediate can be oxidized to obtain a sulfonyl derivative, and the sulfonyl derivative and 2-isopropoxy-5-methyl-4-(piperidine-4-yl)aniline are subjected to condensation to finally obtain 5-chloro-N2-(2-isopropoxy-5-methyl-4-(piperidine-4-yl)phenyl)-N4-(2-(isopropylsulfonyl)phenyl)pyrimidine-2,4-diamine (Ceritinib); and the synthesis method has characteristics of readily available raw materials, high yield, mild reaction, simple operation and low production cost, and is suitable for industrial production.

DEUTERATED DIAMINOPYRIMIDINE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SUCH COMPOUNDS

The present invention related to deuterated diaminopyrimidine compounds and pharmaceutical compositions comprising such compounds. In particular, disclosed are the deuterated diaminopyrimidine compounds shown as formula (I), and the pharmaceutical compositions comprising such compounds or crystal form, pharmaceutically acceptable salts, hydrates or solvates thereof. The compounds of the present invention can be used for treating and/or preventing protein kinase-associated diseases, such as cell proliferative disease, cancer, immune disease and the like.

Imidazoline derivatives as alpha-1A adrenoceptor ligands

Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.

2-(Anilinomethyl)imidazolines as α1 adrenergic receptor agonists: The discovery of α10 subtype selective 2′-alkylsulfonyl-substituted analogues

A series of 2′-alkylthio-2-(anilinomethyl)imidazolines were prepared to examine the effect of the alkyl group size, sulfur oxidation state, and phenyl ring substitution on ligand binding and agonism of α-adrenergic receptor subtypes α1a, α1b, α1d, α2a, and α2c. Binding at all receptor subtypes decreased for compounds in the sulfone oxidation state as compared to their sulfide analogues. While sulfides were generally potent, nonselective agonists, sulfones exhibited α1a subtype selectivity in a cell-based functional assay. Sulfone (32) was 250-7000-fold selective for α1a vs all other subtypes.

Alkyl sulfones

This invention relates to alkyl sulfones which are useful as herbicides and plant growth regulants.

Reaction of Phenylnitrenium Ion with Sulphides. A Novel Synthetic Method for Aminophenyl Sulphide Derivatives

The reaction of phenyl azide with sulphides in the presence of both trifluoroacetic acid and trifluoromethanesulphonic acid to produce 2- and 4-aminophenyl sulphides (2) and (3) was investigated in order to obtain information on the following points: the kinetics of decomposition of phenyl azide, the effect of addition of benzene to reaction systems, the replacement of phenyl azide by 1-phenyl-2-methyl-4,6-diphenylpyridinium salt, and the steric and electronic effect of substituents in the sulphides.The products are formed through an azasulphonium ion by reaction of phenylnitrenium ion with sulphide, followed by rearrangement of the alkyl group in the azasulphonium ion.Sulphides with primary alykl groups larger than propyl result in selective formation of ortho-products (2), the mechanism of which is discussed in detail.