1,2-Dichloroethane → HCID 11960790, compound

Participants

Reaction Steps

A mixture of ethyl 5-(aminomethyl)-1-benzothiophene-2-carboxylate hydrochloride (75 mg, 0.28 mmol), phenylacetyl chloride (0.045 mL, 0.34 mmol) and NEt3 (0.20 mL, 1.4 mmol) in 1 mL of DMF was stirred for 3 h, poured into EtOAc, washed with sat'd NaHCO3, dried (Na2SO4) and concentrated. Next, the residue was dissolved in 2:1:1 THF/MeOH/water (2 mL) and stirred for 3 h in the presence of LiOH (35 mg, 0.83 mmol), then finally poured into EtOAc and washed with 2 N HCl, dried (Na2SO4) and concentrated. The residue was dissolved in DMF (2 mL) and treated with EDC (100 mg, 0.524 mmol), HOBt (50 mg, 0.37 mmol) and 1,2-phenylenediamine (60 mg, 0.56 mmol). After stirring overnight the reaction mixture was poured into EtOAc, washed with sat'd NaHCO3, dried (Na2SO4) and concentrated. Trituration with ether gave the desired product: 1H NMR (600 MHz, DMSO-d6) δ 9.86 (s, 1H), 9.11 (t, J=5.9 Hz, 1H), 8.26 (s, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.88 (d, J=7.0 Hz, 2H), 7.85 (s, 1H), 7.52 (t, J=7.3 Hz, 1H), 7.43-7.47 (m, 3H), 7.14 (d, J=7.0 Hz, 1H), 6.96 (t, J=7.0 Hz, 1H), 6.75 (d, J=7.9 Hz, 1H), 6.57 (t, J=7.3 Hz, 1H), 4.95 (s, 2H), 4.59 (d, J=5.9 Hz, 2H); MS cal'd 416 (MH+), exp 416 (MH+).

Provenance & Evidence