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US 2010/0076189 A1Published application
Process for the preparation of imatinib and intermediates thereof
AssigneeF.I.S. Fabbrica Italiana Sintetici S.p.A.
InventorsAlessandro Falchi, Ennio Grendele, Riccardo Motterle, Mariano Stivanello
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Abstract
It is the object of the present invention a process for the preparation of 4-methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine and analogues thereof, intermediates useful for the synthesis of Imatinib, or 4-[(4-methyl-1-piperazinyl)methyl]-N-[4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]benzamide.
Claims16
A process for the preparation of compounds of Formula 1
- in which R1 represents amino, nitro, halogen, hydroxy, NH(CO)R3, NHR4,
- R3 represents 4-(halo-methyl)phenyl, 4-(hydroxymethyl)phenyl, 4-((4-methylpiperazinyl)carbonyl)phenyl, 4-(alkoxycarbonyl)phenyl, or 4-[(4-methyl-1-piperazinyl)methyl]phenyl, wherein alkoxy means C1-C4 alkoxy,
- R4 represents a protecting group for the amine group,
- comprising the steps of:
- a) reacting the β-oxo-3-pyridinepropanal, a salt thereof, or a enolether thereof of Formula 17
- wherein R2 represents hydrogen, C1-C4 alkyl, benzyl, or phenyl,
- with an aryl guanidine of Formula 3
- wherein R1 has the meaning described above, to yield the compound of Formula 19
- in which R1 has the foregoing meaning, and
- b) cycling the intermediate of Formula 19 in the presence of a base.
7 more elements
The process for the preparation of 4-methyl-N3-[4-(3-pyridinyl)-2-pyrimidinyl]-1,3-benzenediamine of Formula 8
- comprising the steps of:
- a) reacting the sodium salt of the β-oxo-3-pyridinepropanal of Formula 20 (or a tautomer thereof)
- with the (2-methyl-5-aminophenyl)guanidine of Formula 21
- to yield the compound of Formula 22
- and b) cycling the intermediate of Formula 22 in the presence of a base.
2 more elements
Compounds of Formula 19
- wherein R1 represents amino, nitro, halogen, hydroxy, NH(CO)R3, NHR4,
- R3 represents 4-(halo-methyl)phenyl, 4-(hydroxymethyl)phenyl, 4-((4-methylpiperazinyl)carbonyl)phenyl, 4-(alkoxycarbonyl)phenyl, or 4-[(4-methyl-1-piperazinyl)methyl]phenyl, wherein alkoxy means C1-C4 alkoxy, and
- R4 represents a protecting group for the amine group.
15-66. (canceled)
Dependencies are inferred from the claim text.