4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine - CAS 941685-27-4
Catalog number: B0001-452024
Category: Pyrimidines
Molecular Formula:
C15H21N5OSi
Molecular Weight:
315.45
COA:
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Ordering Information
Catalog Number Size Price Stock Quantity
B0001-452024 100 mg $295 In stock
B0001-452024 1 g $598 In stock
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Synonyms:
trimethyl-[2-[[4-(1H-pyrazol-4-yl)pyrrolo[2,3-d]pyrimidin-7-yl]methoxy]ethyl]silane
MSDS:
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InChIKey:
AVMLPTWVYQXRSV-UHFFFAOYSA-N
InChI:
InChI=1S/C15H21N5OSi/c1-22(2,3)7-6-21-11-20-5-4-13-14(12-8-18-19-9-12)16-10-17-15(13)20/h4-5,8-10H,6-7,11H2,1-3H3,(H,18,19)
Canonical SMILES:
C[Si](C)(C)CCOCN1C=CC2=C(N=CN=C21)C3=CNN=C3
1. Enantioselective Synthesis of Janus Kinase Inhibitor INCB018424 via an Organocatalytic Aza-Michael Reaction
Qiyan Lin,* David Meloni. Org. Lett., Vol. 11, No. 9, 2009
Janus kinases (JAKs) are crucial signal transducers for a variety of cytokines, growth factors, and interferons. Inhibition of JAKs has advanced the basic and clinical studies of tyrosine kinase inhibitors as anticancer, anti-inflammation, and antiallograft rejection agents. It has been suggested that inhibition of JAKs can be beneficial for patients with myeloproliferative disorders and inflammatory conditions such as rheumatoid arthritis. INCB018424 was discovered as an inhibitor of JAKs and is currently under clinical development. In view of its structural features, we envisioned that INCB018424 could be prepared from suitable chiral β-amino carbonyl compounds. The catalytic asymmetric aza-Michael reaction is a powerful method for the synthesis of these compounds. Although the use of transition metal complexes with chiral ligands is well-documented, the use of organo-catalysts in asymmetric aza-Michael reactions offers a unique advantage by not requiring metal removal from drug substance in large scale production.
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CAS 941685-27-4 4-(1H-Pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

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