2-Fluoroethyl bromide → benzyl(3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-(2-fluoroethoxy)pyrrolidine-1-carboxylate

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Reaction Steps

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate and 2-fluoro-1-bromo ethane, and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, DMSO-d6) δ) 7.61, 7.38-7.36, 5.85, 5.08, 4.52, 4.50, 4.38, 4.22, 3.75-3.40, 2.60, 2.53, 1.19-1.13; IR (liq.) 2970 (s), 2937 (s), 2340 (w), 2068 (w), 1996 (w), 1954 (w), 1705 (s), 1546 (s), 1499 (s), 1448 (s), 1422 (s), 1395 (s), 1351 (s), 1136 (s), 1107 (s), cm−1; HRMS (FAB) calcd for C22H29FN4O3+H 417.2302, found 417.2299.

Provenance & Evidence