tert-Butyl 4-(4-aminophenyl)piperidine-1-carboxylate → HCID 68677244, compound

Participants

Reaction Steps

Using the procedure outlined in Example 1(g) the title compound was prepared from 4-(4-amino-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (from the previous step, 66 mg, 0.24 mmol) and 8-indan-5-yl-2-methanesulfonyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (from Example 1(e), 100 mg, 0.24 mmol). A yellow solid was obtained (75 mg, 51%) after a preparative HPLC (32 mL/min 5-100% MeCN/H2O gradient over 10 min) purification. The Boc group was removed by treatment with TFA in CH2Cl2 (1:1 v/v) to give the title compound. 1H NMR (400 MHz, CDCl3) δ (ppm): 9.31 (s, 1H), 8.54 (s, 1H), 7.42 (d, J=7.9 Hz, 1H), 7.29 (br, 2H), 7.27 (s, 1H), 7.18 (d, J=7.9 Hz, 1H), 6.91 (br, 2H), 4.35 (q, J=7.1 Hz, 2H), 3.52 (m, 2H), 3.16 (br, 2H), 2.97 (m, 4H), 2.68 (m, 1H), 2.22 (m, 2H), 1.95 (m, 2H), 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence