Isopropylamine → HCID 22181351, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-ethoxy-N-[5-(methylamino)-2-nitrophenyl]-benzeneacetamide (2.20 g, 6.69 mmol) in 1,2-dichloroethane (100 mL) was stirred at room temperature under nitrogen as triphosgene (1.99 g, 6.69 mmol) and TEA (0.93 mL, 6.69 mmol) were added. After 30 minutes, DMAP (817 mg, 6.69 mmol), and isopropylamine (3.42 mL, 40.0 mmol) were added, and the contents were stirred for 16 hours at 45° C. The mixture was quenched with saturated aqueous NaHCO3 (40 m L) and the layers were separated. The aqueous phase was extracted with dichloromethane (2×50 mL) and the organic layers were combined and washed with brine (50 mL), and dried with Na2SO4. The solids were filtered off and the filtrate concentrated in vacuo to a residue which was purified by column chromatography (75% EtOAc, 25% heptane on silica gel) to give the title compound (2.44 g, 88%), 1HNMR (400 MHz, CDCl3): δ 1.14 (d, J=6.4, 6H), 1.38 (t, J=7.1 Hz, 3H), 3.29 (s, 3H), 3.71 (s, 2H), 4.01 (q, J=7:1 Hz, 2H), 4.70 (s, 1H), 6.90 (d, J=8.8 Hz, 2H), 7.00 (dd, J=2.5, 9.2 Hz, 1H), 7.22 (d, J=8.8 Hz, 2H), 8.13 (d, J=9.2 Hz, 1H), 8.61 (d, J=2.5 Hz, 1H). MS (ESI) (M+H)+=415.

Provenance & Evidence