1-(4-Methoxybenzoyl)-piperazine → (4-(2-Amino-5-chloro-3-nitropyridin-4-yl)piperazin-1-yl)(4-methoxyphenyl)methanone

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Reaction Steps

The method followed that used to prepare 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide (Example 1, step 5), but using 2-amino-4,5-dichloro-3-nitropyridine (0.034 g, 0.16 mmol), isopropanol (3.0 ml), and (4-methoxyphenyl)(piperazin-1-yl)methanone (0.055 g, 0.25 mmol). Purification of the crude product on an isolute silica column using a gradient of ethyl acetate in dichloromethane as eluant (10 to 30%) afforded the title compound as a yellow solid (0.038 g, 61%). 1H-NMR (500 Mz, DMSO-d6) 3.13 (br s, 4H, piperazine N(CH2)2), 3.65 (br s, 4H, piperazine N(CH2)2), 3.86 (s, 3H, OCH3), 7.06 (d, J=8.27 Hz, 2H) and 7.47 (d, J=8.21 Hz, 2H) (2,6-C6H4—OMe and 3,5-C6H4—OMe), 7.14 (s, 2H, 2-NH2), 8.19 (s, 1H, 6-H);

Provenance & Evidence