Trifluoroacetic acid → {4-[4-(2-Cyclopropyl-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid

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Reaction Steps

{4-[4-(2-Cyclopropyl-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid was prepared following the general procedures for the synthesis of 2-(4-(4-ethoxybenzoyl)piperidin-1-yl)acetic acid from 2-(4-(4-fluorobenzoyl)piperidin-1-yl)acetic acid and 2-cyclopropyl-ethanol. The title compound (74.3 mg, 0.143 mmol) was prepared following the general procedure of Example 1 from {4-[4-(2-cyclopropyl-ethoxy)-benzoyl]-piperidin-1-yl}-acetic acid and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one. MS (ESI) m/z 495.5 (M+H+); HPLC (Insertsil ODS3 100×3 mm C-18 column: mobile phase: 5-95% acetonitrile/water with 0.1% TFA, at 1 mL/min over 7.75 min.) t=1.51 min. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.07-0.05 (m, 2H), 0.23-0.36 (m, 2H), 0.58-0.75 (m, 1H), 1.47-1.65 (m, 6H), 2.01-2.18 (m, 2H), 2.37 (br. s., 2H), 2.78-2.89 (m, 3H), 3.20 (dd, J=15.41, 6.32 Hz, 2H), 3.69 (t, J=5.56 Hz, 2H), 3.98 (t, J=6.57 Hz, 2H), 4.05 (d, J=5.56 Hz, 2H), 4.20 (s, 2H), 6.90 (d, J=9.09 Hz, 2H), 7.81 (d, J=8.59 Hz, 2H), 8.08 (t, J=5.81 Hz, 1H), 12.24 (br. s., 1H). HRMS calculated for C27H35N4O5: 495.2607 (M+H). found (ESI, [M+H]+): 495.2622.

Provenance & Evidence