4-(Aminomethyl)piperidine → HCID 25123681, compound

Participants

Reaction Steps

4-(9-Cyclopentyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-benzoic acid (35 mg, 0.085 mmol), DIPEA (28 μl, 0.17 mmol, 2 eq) and TBTU (30 mg, 0.093 mmol, 1.1 eq) were added to 3 ml DCM and the resulting solution stirred at rt for 30 min before the addition of 4-aminomethylpiperidine (13 μl, 0.10 mmol, 1.2 eq). The RM was then stirred at rt for 16 h. The RM was concentrated and the product extracted using DCM/H2O. The organic extracts were combined, washed with sat NaCl, dried using MgSO4, filtered and the filtrate evaporated under reduced pressure and further dried in vacuo to give a yellow oily residue (21 mg, 49%); Rt=9.86 min (0—60—20 min, purity 100%); 1H NMR (CD3OD): δ 1.69-1.75 (m, 6H), 1.82 (bs, 2H), 1.96-1.99 (m, 2H), 2.03-2.05 (bs, 2H), 2.18-2.23 (m, 2H), 2.34 (s, 3H, CH3), 2.68 (dd, J=4.5 Hz, 2H, CH2), 2.95-2.97 (m, 2H), 3.28 (s, 3H, CH3), 3.73 (dd, J=4.5 Hz, 2H, CH2), 3.89-3.94 (m, 1H, CH), 4.01 (s, 3H, CH3), 4.91-4.96 (m, 1H, CH), 7.49-7.51 (m, 2H), 8.02 (bs, 1H), 8.50 (d, J=8.5 Hz, 1H, phe-H); MS+ve: 508.2.

Provenance & Evidence