(R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate → (R)-benzyl 4-(3-(1-(3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carboxamido)ethyl)phenyl)piperazine-1-carboxylate

Participants

Reaction Steps

Following the same procedure as described for Example 3, Example 204 (12 mg, 0.022 mmol, 25% yield) was prepared as an off-white powder by using 3-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-4-carbonyl chloride and (R)-benzyl 4-(3-(1-aminoethyl)phenyl)piperazine-1-carboxylate (Intermediate 33). LC-MS (ESI) m/z 541 (M+H), RT=1.64 min (Method C). Orthogonal HPLC (150×4.6 mm 3.5 μm, 254 nm): Sunfire {RT=8.9 min, 95%}; Xbridge {RT=8.5 min, 93%}. 1H NMR (500 MHz, MeOD) δ ppm 7.55 (1 H, d, J=7.7 Hz), 7.46-7.50 (2 H, m), 7.36-7.41 (4 H, m), 7.30-7.34 (3 H, m), 7.26 (1 H, s), 7.22-7.24 (1 H, m), 7.13 (1 H, d, J=7.7 Hz), 7.03 (1 H, dd, J=8.1, 2.1 Hz), 5.28 (1 H, d, J=7.2 Hz), 5.17 (2 H, s), 3.82 (3H, s), 3.71 (4 H, d, J=3.6 Hz), 3.29 (4 H, d, J=5.5 Hz), 1.55 (3 H, d, J=7.2 Hz).

Provenance & Evidence