Dimethylamine, hydrochloride → HCID 89610459, compound

Participants

Reaction Steps

To a solution of triethylammonium 3,4-bis(benzyloxy)-5-(ethoxycarbonyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (5) (10.84 g, 17.99 mmol) in DMF (150 mL), at 0° C. was added HATU (10.26 g, 27.0 mmol), dimethylamine hydrochloride (2.93 g, 36.0 mmol) and DIPEA (18.8 ml, 108 mmol). The reaction mixture was stirred at RT for 16 h and partitioned between EtOAc (500 mL) and 1M HCl (aq.) (250 mL). The organic phase was washed successively with 1M HCl (aq.) (250 mL), sat. NaHCO3 (aq.) (2×250 mL), and brine (2×250 mL), dried (MgSO4), filtered and concentrated in vacuo to afford ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (7.62 g, 79%) as a light yellow oil, that solidified on standing: m/z 529 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 7.51-7.21 (m, 10H), 7.14-7.03 (m, 2H), 6.94-6.84 (m, 2H), 5.12 (s, 2H), 4.96 (s, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.77 (s, 3H), 2.70 (s, 6H), 1.00 (t, J=7.1 Hz, 6H).

Provenance & Evidence