24403-31-4

Upstream product

• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 4799-53-5 ethyl 2(Pyridin-2-yl)acrylate 
• 2739-98-2 ethyl 2-(pyridinyl-2)acetate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

Downstream Products

• 119448-87-2 ethyl imidazo[1,5-a]pyridine-1-carboxylate 

Relevant academic research and scientific papers

Attempts to prepare some 3-substituted azolo[1,2-x]azines, intermediates in the synthesis of azaaplysinopsin derivatives

Some 3-substituted pyrrolo[1,2-a]azines 4a-d were prepared in low yields from the corresponding 2-methylpyridines 1a,b and pyrazine derivatives 1c,d by quaternization with methyl bromoacetate followed by treatment with N,N- dimethylformamide dimethyl acetal. Ethyl 2-pyridinylacetate (5) and 2- pyridinylacetonitrile (6) were converted with 4-(2-bromo-1- dimethylaminoethylidene)-2-phenyl-5(4H)-oxazolone (9) into pyrrolo[1,2- a]pyridine derivatives 10 and 12, intermediates in the synthesis of azaaplysinopsins.

The synthesis and transformations of 2-[2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl]amino-3-dimethylaminopropenoates. The synthesis of substituted β-amino-α,β-didehydro-α-amino acid derivatives

Alkyl (Z)-2-[(E)-2-ethoxycarbonyl-2-(2-pyridinyl)ethenyl] amino-3-dimethylaminopropenoates 7 and 8 were prepared from ethyl 2-pyridinylacetate (1) in two steps. Substitution of the dimethylamino group with alkyl-, aryl-, or heteroarylamines afforded the corresponding β-alkyl- 22-24, β-aryl- 25-35, and β-herteroaryl-amino-α,β-didehydro-α-amino acid 36 and 37 derivatives, intermediates for further preparation of various heterocyclic systems. The orientation around both double bonds were determined by various nmr techniques.

Divergent and Regioselective Synthesis of Pyrazolo[1,5- a]pyridines and Imidazo[1,5- a]pyridines

Nitrogenous heterocycles are ubiquitous in pharmaceuticals and drug-like compounds; however, regioselective synthesis has proved challenging. Herein we report our efforts to develop a regioselective method for the synthesis of pyrazolo[1,5-a]pyridines and the serendipitous discovery of a protocol for the regioselective formation of imidazo[1,5-a]pyridines. Together, these transformations allow for the rapid and selective formation of two important heterocyclic motifs from a common intermediate.

Pyrazolyl derivatives, preparation process and intermediates of this process as medicinal products and pharmaceutical compositions containing them

The present invention relates to the novel derivatives of formula (I) in which A is, if it is present, a (C1-C6) alkyl, a (C3-C6) alkenyl, a (C3-C6) alkynyl, a (C3-C7) cycloalkyl or a (C5-C7) cycloalkenyl, R1 is an NR6R7, (C4-C7) azacycloalkyl, (C5-C7) azacycloalkenyl, (C5-C9) azabicycloalkyl or (C5-C9) azabicycloalkenyl group; A-R1 is such that the nitrogen of R1 and the nitrogen in the 1-position of the pyrazole are necessarily separated by at least two carbon atoms, R3 is an H, halogen, OH, SH, NH2, ORc, SRc, SORa, SO2Ra, NHCHO, NRaRb, NHC(O)Ra, NHC(S)Ra or NHSO2Ra, R4 is an aryl or heteroaryl; and R5 is an H, halogen, CF3, CHF2, CH2F, linear or branched (C1-C6) alkyl or (C3-C7) cycloalkyl to their racemates, enantiomers and diastereoisomers and to their mixtures, their tautomers and to their pharmaceutically acceptable salts.