1,4'-Bipiperidine → HCID 178523850, compound

Participants

Reaction Steps

To a stirred solution of the acid (R)-2-(4-(1,2-dihydro-2-oxoquinazolin-3(4H)-yl)piperidine-1-carboxamido)-3-(2-(trifluoromethyl)-1H-benzo[d]imidazol-5-yl)propanoic acid (33 mg, 0.06 mmol) and diisopropylethylamine (33 mg, 0.25 mmol) in methylene chloride (2 mL) was added a solution of PyBOP (33 mg, 0.06 mmol) and 4-piperidinopiperidine (12 mg, 0.07 mmol) in methylene chloride (1 mL). The reaction mixture was stirred at room temperature for 16 h and was subjected to preparative thin layer chromatography for purification (1:10 2M ammonia in methanol/methylene chloride) to give the title compound (4.6 mg, 12% yield). 1H-NMR (CD3OD, 500 MHz) δ 7.73–7.71 (m, 1H), 7.62 (bs, 1H), 7.39–7.36 (m, 1H), 7.19–7.11 (m, 2H), 6.96 (t, J=7.2 Hz, 1H), 6.81 (d, J=7.9 Hz, 1H), 5.06–5.02 (m, 1H), 4.67–4.58 (m, 1H), 4.49–4.40 (m, 1H), 4.38 (s, 1H), 4.33 (bs, 1H), 4.25–4.16 (m, 2H), 4.10–4.03 (m, 1H), 3.22–3.14 (m, 3H), 3.04–2.87 (m, 4H), 2.79–2.71 (m, 1H), 2.58–2.48 (m, 1H), 2.44–2.33 (m, 1H), 2.31–2.22 (m, 1H), 2.04–1.92 (m, 1H), 1.86–1.42 (m, 11H), 1.33–1.29 (m, 1H), 0.94–0.84 (m, 1H), −0.04–31 0.12 (m, 1H). LC/MS: tR=1.97 min, 681 (MH)+.

Provenance & Evidence