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Linz Design, synthesis and dopamine D4 receptor binding activities of new N heteroaromatic 56 ring

Linz Design, synthesis and dopamine D4 receptor binding activities of new N heteroaromatic 56 ring.M

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4H-pyrrolo[2,3-d]pyrimidin-4-one 34d and the 3-methyl-4H-pyrrolo[3,2-d]pyrimidin-4-ones 49 and 50 with an oxo function.
Furthermore we varied the position of the phenylpiperazinemethyl side chain by these modifications. This variation should
clear up whether the C-6 or C-7 side chain gives an increased affinity to the dopamine D4 receptor (Fig. 1).
2. Results and discussion
2.1. Chemistry
First of all the 7-azaindole (1H-pyrrolo[2,3-c]pyridine) Mannich
base 11 was prepared. We started with 4-methyl-3-nitropyridine2-amine (3)16, which was transformed into the 2-chloro-4-methyl3-nitropyridine (4) by diazotization in hydrochloric acid. The
pyridine 4 has already been synthesized before by nitration but
was received only as an isomeric mixture of 3- and 5-nitro-2chloro-4-picoline.17 Thereafter we ameliorated a variation of the
Leimgruber–Batcho synthesis18 by application of 1-tert-butoxyN,N,N,N-tetramethylmethanediamine (5) instead of N,N-dimethylformamidedimethylacetate in order to receive
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