Potassium Carbonate → Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate (36) (45 mg, 0.09 mmol), 4-(3-chloropropyl)morpholine hydrochloride (19 mg, 0.10 mmol) and K2CO3 (25 mg, 0.18 mmol) in DMF (1 mL) was stirred at 60° C. for 18 h. The reaction mixture was partitioned between EtOAc (10 mL) and water (5 mL), the organic layer was separated and washed with brine (5 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in MeOH (2 mL) and loaded onto a column of SCX (5 g). The column was washed with MeOH and then the product was eluted with 1% NH3 in MeOH, removal of the solvents in vacuo afforded ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate (37) (32 mg, 57%) as a yellow oil: m/z 642 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.47-7.42 (m, 2H), 7.41-7.30 (m, 8H), 7.10-7.05 (m, 2H), 6.99-6.91 (m, 2H), 5.11 (s, 2H), 4.96 (s, 2H), 4.04-3.95 (m, 4H), 3.59-3.52 (m, 5H), 2.72-2.67 (m, 6H), 2.44-2.38 (m, 3H), 2.37-2.32 (m, 5H), 1.92-1.81 (m, 2H), 1.00 (t, J=7.0 Hz, 3H).

Provenance & Evidence