US 2026/0209957 A1Published application

Sequential one-pot synthesis for preparing 4-(4-cyano-2-methoxyphenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide

AssigneeBayer Aktiengesellschaft

InventorsJens AßMANN, Johannes PLATZEK, Marc NOWAKOWSKI, Dirk STORCH

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Abstract

The present invention covers a sequential one-pot synthesis for preparing 4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula (XIII). In particular, in the sequential one-pot synthesis (4R)-4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula ent-(I) is used as starting material to obtain 4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula (XIII) via electrochemical oxidation and electrochemical reduction.

Claims15

Dependent claims

A sequential one-pot synthesis for synthesizing 4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula (XIII)

the synthesis comprising the steps of:
step a) synthesizing 4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,6-naphthyridine-3-carboxamide according to formula (XVII)
via electrochemical oxidation of (4R)-4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula ent-(I)
step b) synthesizing 4-(4-cyano-2-methoxy-phenyl)-5-ethoxy-2,8-dimethyl-1,4-dihydro-1,6-naphthyridine-3-carboxamide according to formula (XIII)
via electrochemical reduction of the compound according to formula (XVII),
wherein in step a) the current density used is decreased or stepwise decreased.

3 more elements

Dependencies are inferred from the claim text.