5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde → 3-(6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidin-2-ylmethyl)-6-cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-4-hydroxy-5,6-dihydro-pyran-2-one

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Reaction Steps

The title compound was prepared analogously to Example B(97) where where 6-Chloro-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde was substituted in place of 5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde and 6-Cyclopentyl-6-{2-[3-fluoro-4-(1-hydroxy-ethyl)-phenyl]-ethyl}-dihydro-pyran-2,4-dione (Example B(115) (was substituted in place of 6-[2-(3-Chloro-5-ethyl-4-methoxy-phenyl)-ethyl]6-cyclopentyl-dihydro-pyran-2,4-dione of that example. 1H NMR (400 MHz, DMSO-d6): δ 1.13 (d, J=6.4 Hz, 3H), 1.23-1.60 (m, 8H), 1.81-1.91 (m, 2H), 2.21-2.25 (m, 1H), 2.40-2.46 (m 3H), 2.6 (d, J=16 Hz, 1H), 3.14 (s, 1H), 3.58 (d, J=16 Hz, 1H), 3.68 (d, J=16 Hz, 1H), 4.78-4.80 (m, 1H), 5.02 (d, J=5 Hz, 1H), 6.75 (d, J=10 Hz, 1H), 6.85 (d, J=7.7 Hz, 1H), 7.23 (t, J=7.70 Hz, 1H), 8.70 (d, J=2.5 Hz, 1H), 9.4 (d, J=2.5 Hz, 1H). Anal. Calcd. For C26H28ClFN4O4.0.5H2O: C, 59.60; H, 5.58; N, 10.69. Found: C, 59.67; H, 5.44; N, 10.65. MS (ESI): 515.2 (M+H)+.

Provenance & Evidence