Diethylamine → HCID 71599636, compound

Participants

Reaction Steps

To a solution of 4-bis(benzyloxy)-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxylic acid (2) (400 mg, 0.85 mmol) and DIPEA (386 μL, 2.11 mmol) in DMF (4 mL) was added HATU (803 mg, 2.11 mmol) followed by diethylamine (219 μL, 2.11 mmol). The reaction mixture was stirred at RT for 1 h and then partitioned between Et2O (50 mL) and sat. NaOAc (aq.) (30 mL). The organic phase was washed succesively with sat. NaOAc (aq.) (20 mL), sat. NaHCO3 (aq.) (20 mL) and brine (2×20 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the crude product. The residue was purified by silica gel chromatography (12 g, 30% EtOAc/isohexane) to afford 3,4-bis(benzyloxy)-N2,N2,N5,N5-tetraethyl-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide (UL1-046) (201 mg, 41%) as a yellow solid: m/z 584 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.47-7.22 (m, 10H), 7.09-6.99 (m, 2H), 6.94-6.76 (m, 2H), 4.97 (s, 4H), 3.74 (s, 3H), 3.29-3.03 (m, 8H), 0.98-0.71 (m, 12H).

Provenance & Evidence