N-[4-[(3-Bromophenyl)amino]-6-quinazolinyl]-2-butynamide

ChEBI: A member of the class of quinazolines that is 4,6-diaminoquinazoine in which the one of the hydrogens attached to the amino group at position 4 has been replaced by a m-bromophenyl group while one of the hydrogens attached to the amino group a position 6 has been replaced by a but-2-ynoyl group.

N-{4-[(3-bromophenyl)amino]quinazolin-6-yl}but-2-ynamide is a member of the class of quinazolines that is 4,6-diaminoquinazoine in which the one of the hydrogens attached to the amino group at position 4 has been replaced by a m-bromophenyl group while one of the hydrogens attached to the amino group at position 6 has been replaced by a but-2-ynoyl group. It has a role as an epidermal growth factor receptor antagonist, an antineoplastic agent and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is a member of quinazolines, a ynamide, a member of bromobenzenes and a secondary carboxamide.

To a solution of 2-butynoic acid (196 mg, 2.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (385 mg, 2.0 mmol) in DMF (5 mL) stirring at 25° C. for 20 minutes was added 6-amino-4-[(3-bromophenyl)amino]quinazoline (316 mg, 1.0 mmol). The resulting solution was stirred under N2 at 25° C. for 14 hours further 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (206 mg, 1.0 mmol) and 2-butynic acid (82 mg, 1.0 mmol) were. After another 8 hours further, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (197 mg, 1.0 mmol) and the acid (93 mg, 1.0 mmol) were added to the reaction. After stirring at 25° C. a further 12 hours, the reaction was quenched with water. The yellow precipitate was collected, sonicated with acetone, treated with triethyl amine and purified by preparative tlc on silica, eluding with 1:1 EtOAc/acetone. The desired product was isolated as a yellow solid (20 mg, 4.7percent), mp 281-283° C. 1H NMR [(CD3)2SO]: δ 10.97 (brs, 1H, NH), 9.93 (s, 1H, NH), 8.76 (s, 1H, H5), 8.57 (s, 1H, H2), 8.14 (s, 1H, H2'), 7.84-7.76 (m, 3H, H7, H8, H4'), 7.34 (t, J=8.1 Hz, 1H, H5'), 7.29 (d, J=7.8 Hz, 1H, H6'), 2.09 (s, 3H, CH3). Mass Spectrum (APCI): 383 (100, 81BrMH+), 382 (23, 81BrM+), 381 (95, 79BrMH+). Calculated for C18H13N4BrO.0.3HCl.0.6C3H6O: C, 55.69; H, 3.99; N, 13.12percent. Found: C, 55.67; H, 3.96; N, 12.93percent.

Molecular Weight:381.2
XLogP3:4.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:380.02727
Monoisotopic Mass:380.02727
Topological Polar Surface Area:66.9
Heavy Atom Count:24
Complexity:514
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes