Dimethylcarbamoyl Chloride → HCID 89610413, compound

Participants

Reaction Steps

Dimethylcarbamic chloride (163 μL, 1.77 mmol) was added dropwise to a stirred suspension of ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-012) (494 mg, 1.42 mmol) and K2CO3 (255 mg, 1.85 mmol) in MeCN (8 mL). The resulting mixture was stirred at RT for 24 h then partitioned between water (30 mL) and DCM (20 mL) the aqueous layer was extracted with DCM (2×20 mL), the combined organics were dried (MgSO4), filtered and solvents removed in vacuo to give an orange oil. The residue was purified by silica gel chromatography (12 g, 0-10% MeOH (+1% NH3) in DCM) to afford ethyl 5-(dimethylcarbamoyl)-4-((dimethylcarbamoyl)oxy)-3-hydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-066) (35 mg, 6%) as a white solid: m/z 420 (M+H)+ (ES+). 1H NMR (400 MHz, DMSO-d6) δ: 8.85 (s, 1H), 7.16-7.06 (m, 2H), 6.95-6.86 (m, 2H), 4.00 (q, J=7.1 Hz, 2H), 3.77 (s, 3H), 2.98 (s, 3H), 2.88 (s, 3H), 2.78 (s, 3H), 2.69 (s, 3H), 1.00 (t, J=7.1 Hz, 3H).

Provenance & Evidence