5-AMINO-5,6,7,8-TETRAHYDROQUINOLINE

To a 20 mL vial was added 5, 6, 7, 8-tetrahy roquinolin-5-amine (500 mg, 3.4 mmol) followed by tert-butoxycarbonyl tert-butyl carbonate (773 mg , 3.5 mmol), 6 mL of tetrahydrofuran, and 6 mL of saturated sodium bicarbonate. The reaction was shaken at room temperature for lh. LCMS showed product formation. The reaction was diluted with ethyl acetate, and washed with water. Organic phase was then concentrated under reduced pressure, The crude product was carried on directly without purification. LCMS M/Z (M+H) 249.A mixture of Z/E)-7, 8-dihydroquinolin-5(6H)-one O-methyl oxime, (Intermediate 23) (1.14 g, 6.47 mmol) in TFA (20 Ml) was added 10% palladium on carbon (10 wt% of Pd/C; 0.15 g) under argon in a Parr shaker flask. The mixture was To 5, 6, 7, 8-tetrahydroquinolin-8-amine (Intermediate 17) (3.0 mmol) in dichloromethane (10 mL) was added chloroethylisocyanate (3.3 mmol). The solution was stirred at room temperature for 1.5 hour. The solvent was removed under vacuum gave a crude material, which was refluxed in H2O (60 mL) for 1 hour. After cooling to room temperature, the reaction was basified with NaOH (pH 14), extracted in Ethyl acetate (3 x 50 mL). The pooled organic layers were washed with brine and dried over magnesium sulphate to give 747. (4, 5-Dihydro-oxazol-2-yl)-(5, 6, 7, 8-tetrahydro- quinolin-8-yl)-amine, 747 as a solid.1HNMR (CDCl3, 300MHz): delta = 6.89-7.34 (m, 4H), 5.21 (s, J= 4.5 Hz, IH), 4.01- 4.07 (m, 2H), 3.34-3.39 (m, 2H), 2.82-2.96 (m, 2H), 2.59-2.67 (m, IH), 1.91-1.99 (m, IH).

Molecular Weight:148.20
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:148.100048391
Monoisotopic Mass:148.100048391
Topological Polar Surface Area:38.9
Heavy Atom Count:11
Complexity:136
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes