1-Adamantanecarboxylic acid → HCID 178495143, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4,5-dimethyl-thiazol-2-ylamine (0.20 g, 1.6 mmol) and 1-bromo-3-methoxypropane (0.28 g, 1.7 mmol) was heated at 85° C. for 14 hours. After cooling to ambient temperature, the unpurified residue (0.31 g, 1.1 mmol) and adamantane-1-carboxylic acid (0.22 g, 1.2 mmol) were processed as described in Example 3B. Purification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient) afforded 0.20 g (50%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.69-1.79 (m, 6H), 1.90-2.00 (m, 6H), 2.00-2.10 (m, 5H), 2.18 (s, 3H), 2.19 (s, 3H), 3.33 (s, 3H), 3.40 (t, J=5.9 Hz, 2H), 4.22 (s, 2H); MS (DCI/NH3) m/z 363 (M+H)+. Anal. Calculated for C20H30N2O2S: C, 66.26; H, 8.34; N, 7.73. Found: C, 66.00; H, 8.60; N, 7.37.

Provenance & Evidence