97651-26-8

Upstream product

• 40219-06-5 benzylidenecyanothioacetamide 
• 141-97-9 ethyl acetoacetate 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 7357-70-2 Cyanothioacetamide 
• 569-37-9 ethyl 3-oxo-2-benzoylbutanoate 

Downstream Products

• 113859-01-1 5-Cyano-2-methyl-6-methylsulfanyl-4-phenyl-nicotinic acid ethyl ester 
• 791843-49-7 ethyl 7-methyl-9-phenyl-2,2-tetramethylene-4-oxo-1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidine-8-carboxylate 
• 111853-43-1 3-amino-5-ethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine-2-carboxamide 
• 148119-00-0 5-Cyano-6-ethylsulfanyl-2-methyl-4-phenyl-nicotinic acid ethyl ester 
• 148119-04-4 5-Cyano-6-methoxycarbonylmethylsulfanyl-2-methyl-4-phenyl-nicotinic acid ethyl ester 
• 113859-07-7 5-Hydroxymethyl-6-methyl-2-methylsulfanyl-4-phenyl-nicotinonitrile 
• 113859-13-5 5-Methoxymethoxymethyl-6-methyl-2-methylsulfanyl-4-phenyl-nicotinonitrile 
• 113859-25-9 6-Methoxymethoxymethyl-7-methyl-5-phenyl-pyrido[2,3-d]pyrimidine-2,4-diamine 
• 113859-19-1 2-Methanesulfonyl-5-methoxymethoxymethyl-6-methyl-4-phenyl-nicotinonitrile 
• 113859-31-7 (2,4-Diamino-7-methyl-5-phenyl-pyrido[2,3-d]pyrimidin-6-yl)-methanol; hydrochloride 
• 113859-41-9 N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamic acid 
• 113859-36-2 diethyl N-pyrimidin-6-yl)methyl>amino>benzoyl>-L-glutamate 
• 148119-12-4 2-Acetyl-3-imino-6-methyl-4-phenyl-2,3-dihydro-thieno[2,3-b]pyridine-2,5-dicarboxylic acid diethyl ester 
• 111853-41-9 (3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl)pyridin-2-ylthioacetamide 

Relevant academic research and scientific papers

REACTIONS WITH CYANOTHIOACETAMIDE DERIVATIVES: SYNTHESIS AND REACTIONS OF SOME PYRAZOLOPYRIDINE DERIVATIVES

The ylidene derivatives of cyanothioacetamide 1a-d reacted with ethyl acetoacetate to give the pyridinethiol derivatives 2a-d.Compounds 2a-d were used as starting material for the synthesis of several heterocyclic compounds.Reaction with hydrazine hydrate, ethyl iodide, methyl chloroacetate and α-chloro ethyl acetoacetate gave the pyridine and annelated pyridine derivatives 5a-d, 6a-d, 7a, 8b-d, and 12a-d, respectively.Compounds 7a, 8b-d and 12a-d reacted with hydrazine hydrate to yield the annelated pyridines 10a-d and 15a-d, respectively.Key words: Cyanothioacetamide; pyridines; thienopyridines; pyrazolopyridines; thienospiropyrazolopyridines.

Chemical synthesis and biological activities of 5-deazaaminopterin analogues bearing substituent(s) at the 5- and/or 7-position(s)

Condensation of cyanothioacetamide (4) with ethyl α-(ethoxymethylene)acetoacetate (5b), ethyl 4-ethoxy-2-(ethoxymethylene)-3-oxobutanoate (5c), ethyl 2-(ethoxymethylene)-3-oxo-4-phenylpropanoate (5d) afforded exclusively the corresponding 6-substituted pyridines (6b-d). Cyclization of 4 with 3-carbethoxybutane-2,4-dione (5e) gave 3-cyano-5-(ethoxycarbonyl)-4,6-dimethylpyridine-2(1H)-thione (6e), whereas reaction of 4 with 3-carbethoxy-1-phenylpropane-1,3-dione (5f) yielded two products, 3-cyano-5-(ethoxycarbonyl)-4-methyl-6-phenylpyridine-2(1H)-thione (6f) and the 6-methyl-4-phenyl isomer 6g. The structural assignments for 6f and 6g are made on the basis of 1H and 13C NMR spectral analyses of the 2-(methylthio)nicotinates (7f,g) prepared from 6f and 6g by treatment with MeI/K2CO3. Nicotinates 7b,d-g were converted into their corresponding 2,4-diaminopyrido[2,3-d]pyrimidines 12b,d-g in five steps, via reduction, protection, oxidation, condensation with guanidine, and deprotection. The 7-mono- and 5,7-disubstituted-5-deazaaminopterins (1b,d-g) were prepared from the respective pyrido[2,3-d]pyrimidines 12b,d-g. Preliminary biological studies showed that 7-methyl and 5,7-dimethyl analogues (1b and 1e) were less active than methotrexate against human leukemic HL-60 and murine L-1210 cells in tissue culture. Compound 1e produced and ILS of 71% at 100 mg/kg per day x 5 (ip) in BDF mice inoculated ip with 106 L-1210 cells.

SYNTHESIS OF 3-CYANO-4-ARYL-5-ETHOXYCARBONYL-6-METHYL-3,4-DIHYDROPYRIDINE-2-THIONES

The condensation of ethyl arylideneacetoacetate with cyanothioacetamide and of arylidenecyanothioacetamides with ethyl acetoacetate or of arylidenecyanothioacetamides with ethyl β-aminocrotonate gave 3-cyano-4-aryl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridine-2-thiones.PMR spectroscopy showed that the 3-cyano-4-aryl-3,4-dihydropyridine-2-thiones are formed as a mixture of cis and trans isomers.