4H-PYRIDO[1,2-A]PYRIMIDIN-4-ONE, 7-METHYL-2-(4-MORPHOLINYL)-9-[1-(PHENYLAMINO)ETHYL]-

TGX-221 is a potent, selective, and cell membrane permeable inhibitor of the PI3K p110β catalytic subunit, used for cancer treatment.

9-(1-anilinoethyl)-7-methyl-2-(4-morpholinyl)-4-pyrido[1,2-a]pyrimidinone is a pyridopyrimidine.

To a suspension of ketone 4 (1 mmol) in toluene (10 mL) was added aniline (3 mmol) and refluxed for 4 h. The reaction mixture was gradually cooled and sodium borohydride (1 mmol) was added at ice-cold temperature. Then reaction mixture was further stirred for 1 h at room temperature. The solution was diluted with dichloromethane (30 mL), the organic layer was washed with water, brine and dried over [NA2S04.] After concentration in vacuo, the residue was purified by column chromatography (silica gel, 3: 1 ethylacetate, petroleum ether) to give pale yellow solid (>60percent yield). 1H NMR (300 MHz, [CDC13)] [6] 8.65 (s, 1H), 7. 58 (s, 1H), (7.11 br t, 2H), 6.68 [(T, ] [J=7.] 5 Hz, 1H), 6.46 (br t, 2H), 5.66 (s, 1H), 5.12 (m, 1H), 4.24 (br s, -NH, 1H), 3. 80 (m, 4H), 3.68 (m, 4H), 2.26 (s, 3H), 1.57 (d, J= 6. 7 Hz, 3H).Using a modified procedure outlined by Jackson et al.To a suspension of ketone 4 (1 mmol) in toluene (10 mL) was added aniline (3 mmol) and refluxed for 4 h. The reaction mixture was gradually cooled and sodium borohydride (1 mmol) was added at ice-cold temperature. Then reaction mixture was further stirred for 1 h at room temperature. The solution was diluted with dichloromethane (30 mL), the organic layer was washed with water, brine and dried over [NA2S04.] After concentration in vacuo, the residue was purified by column chromatography (silica gel, 3: 1 ethylacetate, petroleum ether) to give pale yellow solid (>60percent yield). 1H NMR (300 MHz, [CDC13)] [6] 8.65 (s, 1H), 7. 58 (s, 1H), (7.11 br t, 2H), 6.68 [(T, ] [J=7.] 5 Hz, 1H), 6.46 (br t, 2H), 5.66 (s, 1H), 5.12 (m, 1H), 4.24 (br s, -NH, 1H), 3. 80 (m, 4H), 3.68 (m, 4H), 2.26 (s, 3H), 1.57 (d, J= 6. 7 Hz, 3H).Using a modified procedure outlined by Jackson et al.

Molecular Weight:364.4
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:364.18992602
Monoisotopic Mass:364.18992602
Topological Polar Surface Area:57.2
Heavy Atom Count:27
Complexity:710
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes