(1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol → 2-[((1S)-1-{1-[2-(1-Methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethyl)oxy]-5-[4-(methylsulfonyl)phenyl]pyrazine

Participants

Reaction Steps

The title compound (145 mg, 58%) was prepared from 5-[4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (prepared as in Example 145, Steps 1-2, 125 mg, 0.5 m mol) and (1R)-1-{1-[2-(1-methylethyl)-2H-tetrazol-5-yl]-4-piperidinyl}ethanol (prepared as in Example 190, Step 3, 120 mg, 0.5 mmol) in a manner similar to Example 190, Step 4. Enantiomeric excess was not determined. 1H NMR (400 MHz, DMSO-d6): 8.91 (d, 1H, J=1.4 Hz), 8.41 (d, 1H, J=1.4 Hz), 8.34-8.26 (m, 2H), 8.07-7.99 (m, 2H), 5.13 (quint, 1H, J=6.2 Hz), 4.87 (septet, 1H, J=6.7 Hz), 4.06-3.91 (m, 2H), 3.26 (s, 3H), 2.95-2.78 (m, 2H), 1.96-1.71 (m, 3H), 1.49 (d, 6H, J=6.7 Hz), 1.45-1.35 (m, 2H), 1.32 (d, 3H, J=6.2 Hz); LRMS (ESI), m/z 472 (M+H).

Provenance & Evidence