1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117728727, compound

Participants

Reaction Steps

A mixture of compound 40a (200 mg, 0.421 mmol), N,O-dimethylhydroxylamine hydrochloride (46.1 mg, 0.463 mmol), EDCI (88.7 mg, 0.463 mmol) and DIEA (87.0 μL, 0.505 mmol) in 12 mL of 2:1 DCM/DMF was stirred at rt for 16 h. The mixture was treated with 100 mL of EtOAc and washed with water (2×30 mL), brine (30 mL) and then dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel (0:1-1:1 EtOAc/DCM) to afford compound 65a as a pale yellow solid. 1H-NMR (CDCl3; 400 MHz) δ 8.33 (d, J=8.6 Hz, 2H), 8.07-8.21 (m, 5H), 7.83 (d, J=8.1 Hz, 1H), 7.75 (t, J=7.6 Hz, 1H), 7.53-7.65 (m, 2H), 6.16 (d, J=5.6 Hz, 1H), 4.05 (br. s., 4H), 3.89-4.00 (m, 4H), 2.66 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C29H23N5O2, 474.5 (M+H). found 474.2.

Provenance & Evidence