477600-74-1 Usage
Description
N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine is a chemical compound that serves as an intermediate in the synthesis of (3S,4R)-Tofacitinib (T528010), an enantiopure stereoisomer of the drug Janus kinase 3 (Jak3) inhibitor (CP-690,550). N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine plays a crucial role in the development of pharmaceuticals targeting specific kinases, which are essential in various cellular processes.
Uses
Used in Pharmaceutical Industry:
N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine is used as an intermediate in the synthesis of (3S,4R)-Tofacitinib (T528010) for its role as a Janus kinase 3 (Jak3) inhibitor. The application reason is that it helps in the development of drugs that can inhibit selected members of the STE7 and STE20 subfamily of kinases, which are involved in various cellular processes and are potential therapeutic targets for various diseases.
Used in Research and Development:
In the field of research and development, N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine is used as a key compound in the synthesis of novel Jak3 inhibitors. The application reason is to explore the potential of these inhibitors in treating various diseases by targeting the specific kinases involved in their pathogenesis.
Used in Drug Design and Optimization:
N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine is also used in drug design and optimization processes. The application reason is to improve the potency, selectivity, and pharmacokinetic properties of Jak3 inhibitors, leading to more effective and safer therapeutic options for patients.
Check Digit Verification of cas no
The CAS Registry Mumber 477600-74-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,7,7,6,0 and 0 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 477600-74:
(8*4)+(7*7)+(6*7)+(5*6)+(4*0)+(3*0)+(2*7)+(1*4)=171
171 % 10 = 1
So 477600-74-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H19N5/c1-9-3-5-14-7-11(9)18(2)13-10-4-6-15-12(10)16-8-17-13/h4,6,8-9,11,14H,3,5,7H2,1-2H3,(H,15,16,17)/t9-,11+/m1/s1
477600-74-1Relevant articles and documents
Short enantioselective total synthesis of (+)-tofacitinib
Mane, Kishor D.,Kamble, Rohit B.,Suryavanshi, Gurunath
supporting information, (2021/02/20)
An enantioselective total synthesis of Tofacitinib (CP-690,550), a Janus tyrosine kinase (JAK3) specific inhibitor has been achieved from the readily available 4-piperidone. Proline catalysed hydroxylation is the key step for the synthesis of enantiopure 1-benzyl-4-methylpiperidin-3-ol.
Synthesis method of tofacitinib citrate
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Paragraph 0016; 0032-0033; 0036; 0038-0039; 0042; 0044; ..., (2021/12/07)
The invention discloses a tofacitinib citrate synthesis method, belongs to the technical field of tofacitinib citrate preparation, and can effectively inhibit activity of Janus and JAK1 JAK3, block signal transduction of various inflammatory cytokines, and has an expensive catalyst application in the existing synthesis step. The method uses 1 - benzyl -4 - methyl -3 - (methylamino) piperidine hydrochloride as a raw material to prepare the tofacitinib citrate as a raw material, and then the citric acid tofacitinib citrate is obtained through twice refining 4 -7 - and the - 7H - yield and 2 the 3 - D purity of the tofacitinib citrate are improved.
Preparation method of tofacitinib hydrolysis impurity
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Paragraph 0043-0044, (2021/03/31)
The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of a tofacitinib hydrolysis impurity. The method comprises the following steps: dissolving isopropyl malonate in an organic solvent, adding N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine, conducting stirring at room temperature until the reaction is finished, and recrystallizing the reaction solution to obtain the tofacitinib hydrolysis impurity. The synthesis method provided by the invention is simple, the tofacitinib hydrolysis impurity obtainedby the method is recrystallized for separation, the purity is high, the yield is high, and the impurity compound can be used as an impurity reference substance in tofacitinib finished product detection standards.