Acrylic Acid → HCID 5328419, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-amino-4-[(3-bromophenyl)amino]-benzothieno-quinazoline (130 mg, 0.35 mmol), acrylic acid (0.05 mL, 0.73 mmol), and triethylamine (0.1 mL, 0.72 mmol) in DMF (3 mL) stirred under N2 at 0° C. was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (144 mg, 0.75 mmol). The reaction gradually warmed up to 25° C. and was quenched with water after 20 hours. The formed yellow solid was collected and purified by sonication with acetone to give the desired product (40 mg, 27%), mp 216.4-217.2° C. 1H NMR [(CD3)2SO]: δ10.64 (s, 1H, NH), 9.84 (s, 1H, NH), 8.77 (s, 1H, H2), 8.73 (d, J=1.5 Hz, 1H, H6), 8.31 (d, 1H, J=8.8 Hz, H8), 8.20 (s, 1H, H2′), 7.84 (d, J=8.3 Hz, 1H, H6′), 7.67 (dd, J=8.6, 1.7 Hz, 1H, H9), 7.34 (t, J=7.8 Hz, 1H, H5′), 7.28 (d, J=8.1 Hz, 1H, H4′), 6.50 (dd, J=16.9, 10.0 Hz, 1H, ═CH), 6.34 (dd, J=17.1, 1.7 Hz, 1H, ═CH2), 5.83 (dd, J=10, 1.7 Hz, 1H ═CH2).

Provenance & Evidence