1,2-Dichloroethane → HCID 25014186, compound

Participants

Reaction Steps

A mixture of 6-[(Diethoxyphosphoryl)methyl]nicotinic acid (55.5 mg, 0.188 mmol), tert-butyl [2-amino-4-(2-thienyl)phenyl]carbamate (65.5 mg, 0.226 mmol) HOBT (30.5 mg, 0.226 mmol), and EDC (43.3 mg, 0.226 mmol) was taken into DMF (1.32 mL) and stirred for 3 days. The mixture was diluted with EtOAc and washed with 50% saturated aqueous NaHCO3 3×, brine, dried (MgSO4) and concentrated to afford a residue taken into DCM (2 mL) and TFA (1 mL) and stirred for 1 h. This mixture was concentrated via rotovap, dissolved in minimum MeOH and purified via HPLC (10-100% MeCN in water with 0.025% TFA) to afford fractions poured into saturated aqueous NaHCO3 and extracted with EtOAc 2×. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to afford 36.5 mg of the requisite product as a light yellow solid. 1H NMR (DMSO-d6, 600 MHz) δ 9.84 (s, 1H), 9.04 (s, 1H), 8.26 (dd, J=7.9, 2.0 Hz, 1H), 7.47 (dd, J=8.2, 1.8 Hz, 1H), 7.44 (d, J=2.0 Hz, 1H), 7.33 (dd, J=5.0, 0.9 Hz, 1H), 7.28 (dd, J=8.8, 2.3 Hz, 1H), 7.22 (dd, J=3.5, 1.2 Hz, 1H), 7.2 (dd, J=5.0, 3.5 Hz, 1H), 6.78 (d, J=8.2 Hz, 1H), 5.22 (s, 2H), 3.95 (dt, J=7.3, 7.3 Hz, 4H), 3.53 (d, J=22.3 Hz, 2H), 1.19 Hz (t, J=7.0 Hz, 3H). MS: cal'd 446 (MH+), exp 446 (MH+).

Provenance & Evidence