5-chloro-2-[2-(5-chloro-2,4-dimethoxy-phenyl)ethyl]-2-cyclopentyl-4-hydroxy-3H-pyran-6-one → 6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-3-[(5-chloro-1-methyl-1H-benzimidazol-2-yl)thio]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one

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Reaction Steps

The title compound was prepared analogously to Example C(40), where 3-chloro-6-[2-(5-chloro-2,4-dimethoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one was substituted in place of 3-chloro-6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-4-hydroxy-5,6-dihydro-2H-pyran-2-one and 5-chloro-1-methyl-1H-benzimidazole-2-thiol was substituted in place of 5-chloro-1-isopropyl-1H-benzimidazole-2-thiol. 1H NMR (300 MHz, DMSO-D6) δ: 1.37-1.71 (m, 8H), 2.07-2.19 (m, 2H), 2.35-2.42 (m, 1H), 2.57-2.72 (m, 3H), 2.83-2.88 (m, 1H), 3.71 (s, 3H), 3.75 (s, 3H), 3.86 (s, 3H), 6.71 (s, 1H), 7.01 (d, J=1.70 Hz, 1H), 7.13 (s, 1H), 7.16 (d, J=2.07 Hz, 1H), 7.45 (d, J=8.67 Hz, 1H). ESI-MS calcd for C28H30Cl2N2O5S: 576.1. Found (M+H+): 577.1. Anal. Calcd. For C28H30Cl2N2O5S.1.0H2O: C, 56.47; H, 5.42; N, 4.70; S, 5.38. Found: C, 56.86; H, 5.24; N, 5.05; S, 5.20.

Provenance & Evidence