Trifluoroacetic acid → 2-(4-(4-Propoxybenzoyl)piperidin-1-yl)acetic acid

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Reaction Steps

2-(4-(4-Propoxybenzoyl)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 propan-1-ol. The title compound (76.1 mg, 0.15 mmol) was prepared following the general procedure of Example 1 from 2-(4-(4-propoxybenzoyl)piperidin-1-yl)acetic acid and 2-aminomethyl-3,5,7,8-tetrahydro-pyrano[4,3-d]pyrimidin-4-one. MS (ESI) m/z 469.4 (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=1.39 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99 (t, 3H), 1.60-1.88 (m, 6H), 2.14-2.33 (m, 2H), 2.43-2.65 (m, 4H), 2.98 (br. s., 2H), 3.23-3.42 (m, 1H), 3.83 (br. s., 2H), 3.95-4.10 (m, 2H), 4.20 (br. s., 2H), 4.34 (br. s., 2H), 7.03 (d, J=4.55 Hz, 2H), 7.95 (d, J=4.55 Hz, 2H), 8.22 (br. s., 1H), 12.38 (br. s., 1H). HRMS calculated for C26H33N4O6: 469.2451 (M+H). found (ESI, [M+H]+): 469.2459.

Provenance & Evidence