1260590-51-9

Basic information

• Product Name: N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine dihydrochloride
• Synonyms: N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine dihydrochloride;N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-amine dihydrochloride (N-1 HCl);N-Methyl-N-[(3R,4R)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine x hydrochloride;-4-methylpiperidin-3-yl);N-Methyl-N-((3R,4R);N-METHYL-N-((3R,4R)-4-METHYLPIPERIDIN-3-YL)-7H-PYRROLO[2,3-D]PYRIMIDIN-4-AMINE HCL
• CAS NO: 1260590-51-9
• Molecular Formula: C13H21Cl2N5
• Molecular Weight: 318.24534
• Mol File: 1260590-51-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Aqueous Acid (Slightly, Sonicated), Aqueous Base (Slightly), Water (Slightly)
• CAS DataBase Reference: N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine dihydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine dihydrochloride(1260590-51-9)
• EPA Substance Registry System: N-Methyl-N-((3R,4R)-4-Methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyriMidin-4-aMine dihydrochloride(1260590-51-9)

Safety Data

• Hazardous Substances Data: 1260590-51-9(Hazardous Substances Data)

Usage

Synthesis

Add TFTB-1, sodium hydroxide, ethanol and water to a 20L reaction flask, heat to 85 ° C, and keep the reaction for 3 hours. At the end of the reaction, vacuum distillation at 80-90 ° C until no liquid flows out. Add purified water and continue stirring. The mixture was cooled to room temperature, extracted with dichloromethane, and the aqueous layer was extracted with methylene chloride. The organic layer was combined, and the organic layer was washed with purified water. Filtration, evaporation of the filtrate, addition of acetone, reflux for 30 min, cooling to 20 ° C, filtration, filter cake into a dry box, drying at 60 ° C ± 5 ° C for 4 h, to obtain a white solid, that is, TFTB-2, yield 86%.

Uses

N-Methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-7H-Pyrrolo[2,3-d]pyrimidin-4-amine Hydrochloride, is a substance used in the identification of related substances in the degradation products of tofacitinib citrate using LC-MS technique for process monitoring and quality assurance. A reagent for the synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor.

Application

N-Methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine is a substance used in the identification of related substances in the degradation products of tofacitinib citrate using LC-MS technique for process monitoring and quality assurance. A reagent for the synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor.

Upstream product

• 923036-25-3 (3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine 
• 923036-30-0 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7-p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 479633-63-1 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 1062580-52-2 N-((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methylamine dihydrochloride 
• 1312762-44-9 (3R,4R)-3-methylamino-4-methylpiperidine-1-carboxylic acid tert-butyl ester 
• 374794-77-1 tert-butyl 4-methyl-3-oxopiperidine-1-carboxylate 
• 1121-19-3 4-methylpyridin-3-ol 

Downstream Products

• 1259404-17-5 tasocitinib 
• 540737-29-9 Tofacitinib citrate 

Relevant articles and documents

Preparation method of tofacitinib intermediate

The invention belongs to the field of pharmaceutical chemicals, and relates to a preparation method of a tofacitinib intermediate. According to the preparation method, in the process of preparing a compound shown as a formula II from a compound shown as a

Tofacitinib citrate intermediate as well as preparation method and application thereof

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a tofacitinib citrate intermediate as well as a preparation method and an application thereof. Whereinthe tofacitinib citrate intermediate is N-methyl-N-((3R, 4R)-4-methylpiperidine-3-yl)-7H-pyrrolo [2, 3-D] pyrimidine-4-amine dihydrochloride monohydrate. The preparation method comprises the followingsteps: adding N-methyl-N-((3R, 4R)-1-benzyl-4-methylpiperidine-3-yl)-N-methyl-7H-pyrrolo [2, 3-d] pyrimidine-4-amine into water and an organic solvent, then adding hydrochloric acid and palladium hydroxide carbon, introducing hydrogen to react, and filtering out the palladium hydroxide carbon; cooling to room temperature, dropwise adding an organic solvent, crystallizing, carrying out suction filtration, and drying to obtain the tofacitinib citrate intermediate. The method greatly improves the utilization rate of raw materials, reduces the production cost, and improves the product quality.

Synthetic method for compound

The invention provides a synthetic method for a compound having a structural formula represented by a formula (V) shown in the specification. The method comprises the following steps: 1) performing hydrodebenzylation on a compound having a structural formula represented by a formula (I) shown in the specification to obtain a compound having a structural formula represented by a formula (II) shownin the specification; 2) allowing a compound having a structural formula represented by a formula (III) to be in contact with the compound having the structural formula represented by the formula (II)to obtain a compound having a structural formula represented by a formula (IV) shown in the specification; and 3) allowing the compound having the structural formula represented by the formula (IV) to be in contact with an acid solution to remove t-butoxycarbonyl protection, so as to obtain the compound having the structural formula represented by the formula (V). The synthetic method provided bythe invention has the advantages of a short synthetic route, a simple process, easy availability of the raw materials, simple post-treatment, good quality and a high yield, and is suitable for industrial production of tasocitinib and an intermediate of the tasocitinib.