Ethylamine hydrochloride → HCID 71599802, compound

Participants

Reaction Steps

To a stirred suspension of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (200 mg, 0.38 mmol) and ethylamine hydrochloride (61.7 mg, 0.75 mmol) in THF (2 mL) was added isopropylmagnesium chloride (2 M in THF) (757 μL, 1.51 mmol) and the reaction stirred at RT for 2 h, further portions of ethylamine hydrochloride (120 mg, 1.5 mmol) and isopropylmagnesium chloride (2 M in THF) (1.5 mL, 3.0 mmol) were added and the reaction stirred for 16 h at RT. The reaction mixture was partitioned between sat. NH4Cl solution (aq.) (5 mL) and EtOAc (20 mL) the aqueous was further acidified with 1 M HCl (5 mL). The organic layer was separated and washed with brine (25 mL), dried (MgSO4), filtered and concentrated in vacuo to afford crude product. The residue was purified by silica gel chromatography (25 g, 30-80% EtOAc in isohexane) to afford 3,4-bis(benzyloxy)-N2-ethyl-1-(4-methoxyphenyl)-N5,N5-dimethyl-1H-pyrrole-2,5-dicarboxamide (UL1-055) (192 mg, 95%) as a yellow oil: m/z 528 (M+H)+ (ES+). 1H NMR (400 MHz, CDCl3) δ: 7.44-7.30 (m, 10H), 7.20-7.09 (m, 2H), 7.06-6.97 (m, 1H), 6.89-6.80 (m, 2H), 5.20 (s, 2H), 5.07 (s, 2H), 3.79 (s, 3H), 3.25-3.14 (m, 2H), 2.79 (s, 3H), 2.72 (s, 3H), 0.97 (t, J=7.3 Hz, 3H).

Provenance & Evidence