2-Chloro-4-methoxypyridine → 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxy-1-(4-methoxypyridin-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine hydrogen chloride

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Reaction Steps

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(3R,4S)-4-ethoxy-1-(1,3-thiazol-2-yl)pyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine but substituting 5-(2-chloro-4-methoxyphenyl)-N-[(3R,4S)-4-ethoxypyrrolidin-3-yl]-3,6-diethylpyrazin-2-amine and 2-chloro-4-methoxypyridine provided the title compound as an amporphous solid: 1H NMR (400 MHz, CDCl3) δ 8.6, 8.08, 7.22, 7.12, 7.05, 6.90, 6.40, 5.92, 5.40, 5.00, 4.32, 4.20–4.10, 3.95, 3.86, 3.52, 2.81, 2.60, 1.33, 1.26, 1.18; IR (diffuse reflectance) 2966, 2934, 2685 (b), 2036 (w), 1974 (w), 1657, 1607 (s), 1493, 1463, 1442, 1404, 1293, 1265, 1232, 826 cm−1 HRMS (ESI) calcd for C27H34N5O3Cl+H1 512.2429. found 512.2417.

Provenance & Evidence