Preparation of azinomethyl-rifamycins

Details Preparation of azinomethyl-rifamycins Preparation of azinomethyl-rifamycins

C - Chemistry, Metallurgy

07

D

260/235.82

C07D 498/08 (2006.01)

Patent

CA 1204740

ABSTRACT OF THE DISCLOSURE Azinomethyl-rifamycins I (I) Image wherein Y=H or COCH3 and either R1=C1-C7 alkyl or C3-C4 alkenyl and R2=C1-C7 alkyl, C2-C4 cloro-, hydroxy-, or alkoxy- alkyl C3-C4 alkenyl, cycloalkyl having a C3-C7 ring, cycloalkyl-alkyl having a C3-C6 ring, phenyl or C7-C8 aralkyl optionally monohalogen substituted in the aryl group or NR1R2= a cyclic moiety, said moiety being pyrrolidinyl, piperidinyl, hexahydroazepinyl or heptahydroazocinyl, each of which are unsubstiiuted or substituted with 1 or 2 methyl radicals, 4-alkyl-1-piperazinyl, morpholinyl or 1,2,3,4- tetrahydroisoquinolinyl are prepared from rifamycin S by (a) dissolving the rifamycin S in tetrahydrofuran, CHC13, dioxan, CH2C12 or dichloroethane (b) adding (i) a Schiff's base CH2=NR3 wherein R3= t-alkyl or (ii) a compound R4N(CH2OR5)2 wherein R4=lower alkyl, lower alkenyl, cycloalkyl having a C5-C6 ring, phenyl, benzyl or .alpha.- or .beta.-phenethyl and R5=H or lower alkyl or (iii) a compound Abstract continued.... Image wherein R6=C1-C6 alkyl, cycloalkyl having a C5-C6 ring or alkenyl (c) adding hydrazine and (d) adding a chloroformiminium chloride Image wherein R1 and R2 are as above defined.

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