Trifluoroacetic acid → 2-[4-(4-Cyclopropylmethoxy-benzoyl)-piperidin-1-yl]-acetic acid

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Reaction Steps

2-[4-(4-Cyclopropylmethoxy-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 cyclopropyl-methanol. The title compound (44.7 mg, 0.088 mmol) was prepared following the general procedure of Example 1 from 2-[4-(4-cyclopropylmethoxy-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 481.5 (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=1.27 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.26-0.41 (m, 2H), 0.48-0.68 (m, 2H), 1.14-1.29 (m, 1H), 1.65-1.83 (m, 4H), 2.18-2.33 (m, 2H), 2.51 (br. s., 2H), 2.84-3.08 (m, 3H), 3.32 (br. s., 2H), 3.83 (br. s., 2H), 3.91 (d, J=6.06 Hz, 2H), 4.20 (br. s., 2H), 4.34 (br. s., 2H), 7.03 (d, J=7.07 Hz, 2H), 7.94 (d, J=7.58 Hz, 2H), 8.21 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C26H33N4O5: 481.2451 (M+H). found (ESI, [M+H]+): 481.2459.

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