389090-45-3

Upstream product

• 3173-56-6 benzyl isothiocyanate 
• 1187-42-4 diaminomaleonitrile 
• 18514-52-8 2,3-diaminomaleonitrile 
• 193808-98-9 N-[(Z)-2-amino-1,2-dicyanovinyl]-N'-(4'-cyanophenyl)formamidine 

Downstream Products

• 389090-57-7 5-amino-1-benzyl-4-cyanoformimidoyl-imidazole-2-one 
• 958602-02-3 9-benzyl-8-oxo-2-(pyridin-3-yl)-8,9-dihydro-7H-purine-6-carboxamide 
• 1265321-85-4 9-benzyl-2-(4-hydroxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carbonitrile 
• 1265321-82-1 9-benzyl-2-(4-cyanophenyl)-8-oxo-8,9-dihydro-7H-purine-6-carbonitrile 
• 1265321-79-6 9-benzyl-2-(4-methoxyphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carbonitrile 
• 1265321-74-1 9-benzyl-2-(4-methylphenyl)-8-oxo-8,9-dihydro-7H-purine-6-carbonitrile 

Relevant academic research and scientific papers

HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND USE THEREOF AS PROTEIN KINASE INHIBITORS

Provided herein are Heteroaryl Compounds having the following structure: (I) wherein R1, R2, L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

Efficient synthesis of 4,4′-Bi-1H-imidazol-2-ones from 5-amino-α-imino-1H-imidazole-4-acetonitriles and isocyanates

Reactions of 5-amino-α-imino-1H-imidazole-4-acetonitriles 1 with alkyl and aryl isocyanates led to efficient syntheses of 5′-amino-5-imino-4,4′-bi-1H-imidazol-2-ones 3 formed by intramolecular cyclization of the corresponding 5-amino-α-(N-alkyl/arylcarbamoyl)imino-1H-imidazole-4-acetonitriles 2. The cyclization occurs only slowly in solution but is considerably accelerated by the addition of a catalytic amount of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The reaction of the N-arylamidine 6b, the synthetic precursor of the imidazole 1b, with benzyl isocyanate also led to the formation of 4,4′-bi-1H-imidazol-2-one 3b in quantitative yield. The imidazole intermediate 2b has been isolated and found to be identical with the compound obtained by reaction of the imidazole 1b and benzyl isocyanate. The N-arylamidine 6c (R = 4-NCC6H4) reacted with benzyl isocyanate in a similar way, but the electrophilicity of the amidine carbon atom resulted in rapid hydrolysis of the intermediate 7c leading ultimately to the isolation of the urea 9. The N-alkylamidines 6a and 6d behaved differently in their reaction with benzyl isocyanate, and the major product isolated in these reactions is again the urea 9.

The reactions of diaminomaleonitrile with isocyanates and either aldehydes or ketones revisited

A reinvestigation of the reactions of urea derivatives of diaminomaleonitrile 2 with aldehydes or ketones in the presence of triethylamine has established that the products of these reactions are not pyrimidino[5,4-d]pyrimidines 9 as previously reported, but 8-oxo-6-carboxamido-1,2-dihydropurines 12, which are oxidized rapidly in air to the corresponding 6-carboxamidopurines 13. Similarly, the reaction of Schiff base derivatives of DAMN 5 with isocyanates in the presence of triethylamine gives the substituted 2-oxoimidazoles 20 and not the pyrimidine derivatives 8 as previously claimed. The compounds 20 cyclize in solution and are easily oxidized to 8-oxopurine-6-carbonitriles 22, which give the same 8-oxopurine-6-carboxamides 13 upon further hydrolysis.