Triethylamine → HCID 10194416, compound

Participants

Reaction Steps

Diketene (0.0590 ml, 0.648 mmol) is added dropwise to a solution of 2-[4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluorophenyl]-4H-[1,3,4]thiadiazin-5-one (0.200 g, 0.617 mmol) and triethylamine (0.0946 ml, 0.679 mmol) in DMF (2 ml) and is stirred overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is purified by PTLC (10% MeOH/DCM) to give a white solid (0.22 g, 89%); 1HNMR (300 MHz, DMSO-d6) δ 2.08 (s, 3H), 3.34 (s, 2H), 3.42-3.54 (m, 2H), 3.59 (s, 2H), 3.78 (dd, J=6.3, 9.1 Hz, 1H), 4.14 (t, J=9.1 Hz, 1H), 4.75-4.83 (m, 1H), 7.37 (dd, J=2.2, 8.5 Hz, 1H), 7.52 (dd, J=2.2, 14 Hz, 1H), 7.69 (t, J=8.8 Hz, 1H), 8.45 (t, J=5.8 Hz, 1H), 11.6 (s, 1H); mp 176-8; MS (m/z): [M+H]+=409.

Provenance & Evidence