N-methyl-N-phenyl-2-(piperazin-1-yl)acetamide → 2-[4-(2-Amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-methyl-N-phenyl-acetamide

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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 6, Steps 1 to 6), but using 2-amino-4,5-dichloro-3-nitropyridine (0.036 g, 0.17 mmol), isopropanol (4.0 ml), and N-methyl-N-phenyl-2-piperazin-1-yl-acetamide (0.056 g, 0.24 mmol). Work-up and purification as described for 2-[4-(2-amino-5-chloro-3-nitro-pyridin-4-yl)-piperazin-1-yl]-N-thiazol-2-yl-acetamide afforded the title compound as an orange solid (0.039 g, 57%), 1H-NMR (500 Mz, DMSO-d6) 2.50 (obscured by DMSO peak, piperazine N(CH2)2), 2.96 (br s, 4H, piperazine N(CH2)2), 3.18 (s, 3H, NCH3), 6.94 (s, 2H, NH2), 7.35 (m, 3H) and 7.42 (m, 2H) (N-Ph), 8.05 (s, 1H, pyridine 6-H); LC-MS (ESI, m/z) 3.30 min—405, 407 [(M+H)+, Cl isotopic pattern].

Provenance & Evidence