138343-75-6

Usage

InChI:InChI=1/C11H16N2O2/c1-8-6-5-7-12-9(8)13-10(14)15-11(2,3)4/h5-7H,1-4H3,(H,12,13,14)

Upstream product

• 1603-40-3 3-methylpyridin-2-ylamine 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 149489-03-2 tert-butyl (3-ethylpyridin-2-yl)carbamate 
• 23612-48-8 2-methyl-1H-pyrrolo[2,3-b]pyridine 
• 271-63-6 7-Azaindole 
• 918514-78-0 2-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine 
• 1206846-31-2 C₁₉H₂₁N₃O₂ 
• 1296889-79-6 11-fluoro-7,7-dimethyl-6-oxo-6,7-dihydro-5H-8-oxa-1,13-diazadibenzo[a,d]cyclononene-13-carboxylic acid tert-butyl ester 
• 1296889-80-9 2-[1-(2,4-difluorophenoxy)-1-methylethyl]-2-hydroxy-2,3-dihydropyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 
• 1296889-81-0 2-[1-(2-fluorophenoxy)-1-methylethyl]-2-hydroxy-2,3-dihydropyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 
• 1296889-64-9 7-azaindolo[2,1-c]-6-fluoro-[1,4]benzoxazine 
• 1296889-73-0 2-(2,4-difluorophenoxymethyl)-1H-pyrrolo[2,3-b]pyridine 
• 1296889-74-1 2-cyclohex-1-enyl-1H-pyrrolo[2,3-b]pyridine 
• 1296889-65-0 7-azaindolo[2,1-c]-(6-fluoro-2,2-spirocyclohexyl)-[1,4]benzoxazine 
• 1037253-14-7 5-bromo-3-ethylpyridin-2-amine 
• 1408481-04-8 2-(2-aminopyridin-3-yl)-1-(2,3-dichlorophenyl)ethanol 

Relevant academic research and scientific papers

Iridium- and rhodium-catalyzed dehydrogenative silylations of C(sp 3) - H bonds adjacent to a nitrogen atom using hydrosilanes

Now that is just silylated: In the presence of iridium or rhodium catalysts, C(sp3) - H bonds adjacent to a nitrogen atom were silylated by the aid of a pyridine-directing group. In iridium catalysis, a hydrogen-trapping reagent such as norbornene or tert-butylethylene, which is usually required in late transition-metal-catalyzed dehydrogenative coupling reactions, was not required. In rhodium catalysis, however, 1 equivalent of COD (1,5-cyclooctadiene) was necessary to induce higher conversion. Copyright

Synthesis, Crystal Structure and Inhibitory Activities of 2-(N-Tert-Butoxycarbonylamino)Pyridine Derivatives

Abstract: 2-(N-tert-butoxycarbonylamino) pyridine and 2-(N-tert-butoxycarbonylamino)-3-methylpyridine were synthesized in a one-step method using either 2-aminopyridine or 2-amino-3-methyphyridine with tert-butylcarbonyl anhydride as the starting materials. The products were characterized by single-crystal X-ray diffraction, 1H NMR, 13C NMR, and HRMS. The biological activity of the two compounds against five fungi was determined. 2-(N-tert-butoxycarbonylamino) pyridine has more than 50% inhibitory activity against Pyricularia oryzae, Colletotrichum gloeosporioides, and Alternaria alternate. In addition, the inhibitory activity of 2-(N-tert-butoxycarbonylamino)-3-methylpyridine against Alternaria alternate reached 67.69%. Graphic Abstract: Two 2-BOC aminopyridine derivatives were synthesized and structurally characterized by 1H NMR, 13C NMR, HRMS analysis and X-ray crystal diffraction. The inhibitory activity both compounds was studied. [Figure not available: see fulltext.]

Design and synthesis of novel pyrrolo[2,3-b]pyridine derivatives targeting V600EBRAF

Several pyrrolo[2,3-b]pyridine-based B-RAF inhibitors are well known and some of them are currently FDA approved as anticancer agents. Based on the structure of these FDA approved V600EB-RAF inhibitors, two series of pyrrolo[2,3-b]pyridine scaffold were designed and synthesized in attempt to develop new potent V600EB-RAF inhibitors. The 38 synthesized compounds were biologically evaluated for their V600EB-RAF inhibitory effect at single dose (10 μM). Compounds with high percent inhibition were tested to determine their IC50 over V600EB-RAF. Compounds 34e and 35 showed the highest inhibitory effect with IC50 values of 0.085 μM and 0.080 μM, respectively. Headed for excessive biological evaluation, the synthesized derivatives were tested over sixty diverse human cancer cell lines. Only compound 35 emerged as a potent cytotoxic agent against different panel of human cancer cell lines.

PHENYL AND PYRIDINYL SUBSTITUTED IMIDAZOLES AS MODULATORS OF RORyT

The present invention comprises compounds of Formula I. wherein: R1, R2, R3, R4, R5, Ra, Rb, Q1, and Q2 are defined in the specification. The invention also comprises a method of treating or ameliorating a ROR-γ-t mediated syndrome, disorder or disease, including wherein the syndrome, disorder or disease is selected from the group consisting of rheumatoid arthritis, psoriatic arthritis, and psoriasis. The invention also comprises a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of Formula I.

Synthesis method of 5-chloro-7-azaindole

The invention provides a synthesis method of 5-chloro-7-azaindole. The synthesis method comprises the following steps: (1) reacting a dilithium initiator and trimethylbromosilane to prepare silicon-containing organic lithium; (2) reacting 2-amino-3-methylpyridine and di-tert-butyl dicarbonate to prepare 2-N-BOC-amino-3-methylpyridine; (3) performing lithiation on the 2-N-BOC-amino-3-methylpyridine through the silicon-containing organic lithium, and performing delithiation activation, cyclization and dehydration to prepare 7-azaindole; (4) performing hydrogenation reduction reaction on the 7-azaindole to generate 2,3-dihydro-7-azaindole; (5) performing chlorination reaction on the 2,3-dihydro-7-azaindole through liquid chlorine to generate 5-chloro-2,3-dihydro-7-azaindole; and (6) performing dehydrogenation reaction on the 5-chloro-2,3-dihydro-7-azaindole to obtain 5-chloro-7-azaindole. The synthesis method provided by the invention has the advantages of mild conditions and high yield.

Azonia Aromatic Cations by Ring-Closing Metathesis: Synthesis of Azaquinolizinium Cations

A strategy based on a ring-closing metathesis (RCM) reaction of pyridinium azadienes in the presence of the second generation Grubbs catalyst was employed as a new approach to synthesize the 1-azaquinolizinium (pyrido[1,2-a]pyrimidin-5-ium) heterocycle and some simple derivatives. This method was also successfully applied to the first reported synthesis of the benzo-1-azaquinolizinium (pyrimido[2,1-a]isoquinolinium) cation by using the Hoveyda-Grubbs catalyst in Cl2CHCHCl2 at 130 C.

Aminoazabenzimidazoles, a Novel Class of Orally Active Antimalarial Agents

Whole-cell high-throughput screening of the AstraZeneca compound library against the asexual blood stage of Plasmodium falciparum (Pf) led to the identification of amino imidazoles, a robust starting point for initiating a hit-to-lead medicinal chemistry effort. Structure-activity relationship studies followed by pharmacokinetics optimization resulted in the identification of 23 as an attractive lead with good oral bioavailability. Compound 23 was found to be efficacious (ED90 of 28.6 mg·kg-1) in the humanized P. falciparum mouse model of malaria (Pf/SCID model). Representative compounds displayed a moderate to fast killing profile that is comparable to that of chloroquine. This series demonstrates no cross-resistance against a panel of Pf strains with mutations to known antimalarial drugs, thereby suggesting a novel mechanism of action for this chemical class.

Discovery and characterization of NVP-QAV680, a potent and selective CRTh2 receptor antagonist suitable for clinical testing in allergic diseases

Optimization of a 7-azaindole-3-acetic acid CRTh2 receptor antagonist chemotype derived from high throughput screening furnished a highly selective compound NVP-QAV680 with low nM functional potency for inhibition of CRTh2 driven human eosinophil and Th2 lymphocyte activation in vitro. The molecule exhibited good oral bioavailability in the rat, combined with efficacy in rodent CRTh2-dependent mechanistic and allergic disease models and was suitable for clinical development.

PYRIDAZINE AMIDE COMPOUNDS

The present invention relates to the use of novel triazolopyridine derivatives of formula I: wherein all variable substituents are defined as described herein, which are SYK inhibitors and are useful for the treatment of auto-immune and inflammatory diseases.

Novel Heterocyclic Compounds and Uses Thereof

New substituted heterocyclic compounds, compositions containing them, and methods of using them for the inhibition of Raf kinase activity are provided. The new compounds and compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.