479633-63-1

Basic information

• Product Name: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE
• Synonyms: 4-CHLORO-7-[(4-METHYLPHENYL)SULFONYL]-7H-PYRROLO[2,3-D]PYRIMIDINE;4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE;4-Chloro-7-tosyl-7H-pyrro...;4-Chloro-7-[(4-methylbenzene)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine;4-Chloro-7-p-toluenesulphonyl-7H-pyrrolo[2,3-d]pyrimidine;7H-Pyrrolo[2,3-D]pyriMidine,4-chloro-7-[(4-Methylphenyl)sulfonyl]-;Tofacitinib Impurity R;4-Chloro-7-(p-tolylsulfonyl)pyrrolo[2,3-d]pyrimidine
• CAS NO: 479633-63-1
• Molecular Formula: C₁₃H₁₀ClN₃O₂S
• Molecular Weight: 307.76
• EINECS: 1312995-182-4
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 479633-63-1.mol

Chemical Properties

• Melting Point: 145.0 to 149.0 °C
• Boiling Point: 505.3 °C at 760 mmHg
• Flash Point: 259.4 °C
• Appearance: /
• Density: 1.49
• Vapor Pressure: 2.46E-10mmHg at 25°C
• Refractive Index: 1.696
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 1.73±0.30(Predicted)
• CAS DataBase Reference: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(479633-63-1)
• EPA Substance Registry System: 4-CHLORO-7-TOSYL-7H-PYRROLO[2,3-D]PYRIMIDINE(479633-63-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 479633-63-1(Hazardous Substances Data)

Usage

Uses

4-Chloro-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine is a reagent in the synthesis of (+)-tofacitinib, a selective Janus kinase 3 inhibitor (JAK3) and an immunosuppressant drug.

InChI:InChI=1/C13H10ClN3O2S/c1-9-2-4-10(5-3-9)20(18,19)17-7-6-11-12(14)15-8-16-13(11)17/h2-8H,1H3

Upstream product

• 7400-06-8 4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine 
• 3680-71-5 Allopurinol 
• 52133-67-2 ethyl 2-cyano-4,4-diethoxybutyrate 
• 1634-04-4 tert-butyl methyl ether 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1236033-25-2 (E)-6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine 
• 14160-93-1 4-amino-6-chloro-pyrimidine-5-carbaldehyde 
• 90213-66-4 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine 
• 773076-83-8 2-cyano-4,4-dimethoxybutyric acid ethyl ester 
• 3680-69-1 6-chloro deazapurine 

Downstream Products

• 911122-34-4 4-(2-chloro-imidazol-1-yl)-7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 1346175-13-0 4-[4-(4-fluorophenyl)-1-(methoxymethyl)-2-phenyl-1H-imidazol-5-yl]-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1607005-81-1 {4-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]benzyl}carbamic acid tert-butyl ester 

Relevant articles and documents

Identification of N-Phenyl-7 H-pyrrolo[2,3- d]pyrimidin-4-amine Derivatives as Novel, Potent, and Selective NF-κB Inducing Kinase (NIK) Inhibitors for the Treatment of Psoriasis

A series of N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives with NF-κB inducing kinase (NIK) inhibitory activity were obtained through structure-based drug design and synthetic chemistry. Among them, 4-(3-((7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)-4-morpholinophenyl)-2-(thiazol-2-yl)but-3-yn-2-ol (12f) was identified as a highly potent NIK inhibitor, along with satisfactory selectivity. The pharmacokinetics of 12f and its ability to inhibit interleukin 6 secretion in BEAS-2B cells were better than compound 1 developed by Amgen. Oral administration of different doses of 12f in an imiquimod-induced psoriasis mouse model showed effective alleviation of psoriasis, including invasive erythema, swelling, skin thickening, and scales. The underlying pathological mechanism involved attenuation of proinflammatory cytokine and chemokine gene expression, and the infiltration of macrophages after the treatment of 12f. This work provides a foundation for the development of NIK inhibitors, highlighting the potential of developing NIK inhibitors as a new strategy for the treatment of psoriasis.

PROCESS AND INTERMEDIATES FOR PREPARING A JAK1 INHIBITOR

The present invention is related to processes for preparing itacitinib, or a salt thereof, and related synthetic intermediates related thereto.

PROCESS AND INTERMEDIATES FOR PREPARING A JAK INHIBITOR

The present invention is related to processes for preparing ruxolitinib, or a salt thereof, and related synthetic intermediates related thereto.

Preparation method of key intermediate of JAK inhibitor

The invention discloses a preparation method of a key intermediate of a JAK inhibitor. The preparation method comprises the following steps: step a, protecting an amino group of a raw material 4-chloro-7H-pyrrole-[2.3-d]-pyrimidine to synthesize 4-chloro-

Selective JAK1 inhibitor compound as well as preparation method and application thereof

The invention provides a heterocyclic compound serving as a JAK1 inhibitor and synthesis and use methods, and particularly provides a compound shown as a formula (I), a preparation method of the compound and application of the compound serving as a JAK1 i

COMPOUND HAVING TRKA INHIBITORY ACTIVITY AND PHARMACEUTICAL COMPOSITION, FOR PREVENTING OR ALLEVIATING PAIN, CONTAINING SAME AS ACTIVE INGREDIENT

The present invention relates to a compound having TrkA inhibitory activity and a pharmaceutical composition for preventing or treating pain containing the same as an active ingredient. The compound provided in one aspect of the present invention has excellent TrkA inhibitory activity and exhibits excellent pain inhibitory effects in an animal model of pain after a surgery, and thus can be effectively used as an analgesic.

PROCESS FOR PREPARATION OF ABROCITINIB

The present invention relates to crystalline abrocitinib characterized by X-ray powder diffraction (XRPD) spectrum having peak reflections at about 12.9, 14.7, 19.4, 23.2 and 25.2 ±0.2 degrees 2 theta, and process for its preparation. The present invention relates to amorphous solid dispersion comprising abrocitinib or salt thereof together with at least one pharmaceutically acceptable carrier and process for its preparation.

TRICYCLIC JANUS KINASE 1 INHIBITORS, AND COMPOSITIONS AND METHODS THEREOF

Provided are novel class of therapeutics that are safe and effective inhibitors of Janus kinase 1 and pharmaceutical composition and methods of preparation and use thereof in the treatment of various diseases and disorders (e. g., inflammatory diseases, immune-mediated diseases or cancer).

A class of pyrrolopyrimidine derivatives, and synthesis method thereof

The invention discloses a class of pyrrolopyrimidine derivatives, wherein the pyrrolopyrimidine derivative has a structural general formula represented by a formula (I). The invention also discloses asynthesis method of the compound represented by the for

PROCESS FOR PREPARATION OF TOFACITINIB AND PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

The present invention relates to an improved process for preparation of tofacitinib (I) and pharmaceutically acceptable salt thereof. (I)