Triethylamine → HCID 67951138, compound

Participants

Reaction Steps

Ethyl 4-(2-iodoacetyl)piperazine-1-carboxylate (200 mg, 0.61 mmol) was added to a suspension of benzothiazolone 1 (102 mg, 0.67 mmol), Et3N (233 mg, 1.83 mmol) and Cs2CO3 (198 mg, 0.61 mmol) in anhydrous CH2Cl2 (8 mL) at room temperature. The mixture was stirred for 26 h, and washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:2) to give the title compound (134 mg, 63% yield). The purity of product was 99.3% as shown by HPLC on an HC-C18 column (Agilent, 4.6×250 mm, 5 μM), tR=11.87 min (gradients of 20-90% aqueous CH3CN in 20 min). C16H19N3O4S; white solid; mp 158-160° C.; 1H NMR (400 MHz, CDCl3) δ 8.09 (1H, dd, J=7.2 Hz, 0.8 Hz), 7.59 (1H, m), 7.53 (1H, dd, J=7.2, 0.8 Hz), 7.38 (1H, m), 4.69 (2H, s), 4.13 (2H, q, J=7.2 Hz), 3.60 (2H, m), 3.55 (2H, m), 3.48 (4H, m), 1.25 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3) δ 164.6, 154.6, 140.8, 131.8, 130.0, 126.4, 125.1, 122.9, 120.0, 61.9, 45.3, 45.0, 43.5 (2×), 42.2, 15.0; ESI-HRMS calcd for C16H19N3O4S: 372.0994. found: m/z 372.0992 [M+H]+.

Provenance & Evidence