Triethylamine → HCID 69938070, compound

Participants

Reaction Steps

A solution of 4-fluorobenzoic acid (100 mg, 0.71 mmol) in SOCl2 (2 mL) was stirred at reflux for 1 h. Excess SOCl2 was removed and the residue was dissolved in THF (10 mL). The solution was added to a mixture of Et3N (1 mL) and 3-amino-8,9,10,11-tetrahydro-6H-azocino[2,1-b]quinazolin-13(7H)-one (22 mg, 0.09 mmol). After stirring for 1 h, the mixture was diluted with H2O (30 mL) and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by column chromatography to give the desired product (2 mg). MS (ESI): 366 (MH+); 1H NMR (300 MHz, CDCl3) δ 8.28 (d, J=8.70 Hz, 1H), 7.96-7.91 (m, 4H), 7.75-7.71 (dd, J=8.72 Hz, 2.12 Hz, 1H), 7.24-7.19 (t, J=8.60 Hz, 2H), 4.34 (broad, 2H), 3.06-3.02 (m, 2H), 1.99-1.87 (m, 4H), 1.68-1.66 (m, 2H), 1.47-1.46 (d, J=4.32 Hz, 2H). mGluR5 PAM EC50: +.

Provenance & Evidence