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

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Reaction Steps

{4-[4-(2-Methoxy-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-methoxy-ethanol. The title compound (190 mg, 0.373 mmol) was prepared following the general procedure of Example 1 from {4-[4-(2-methoxy-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 484.8 (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=1.46 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51-1.83 (m, 6H), 2.20-2.33 (m, 2H), 2.51 (br. s., 2H), 2.92-3.03 (m, 4H), 3.24-3.41 (m, 4H), 3.65-3.71 (m, 2H), 3.82 (t, J=5.31 Hz, 2H), 4.16-4.24 (m, 2H), 4.34 (s, 2H), 7.05 (d, J=8.59 Hz, 2H), 7.95 (d, J=8.59 Hz, 2H), 8.24 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C25H33N4O6: 485.2400 (M+H). found (ESI, [M+H]+): 485.2394.

Provenance & Evidence