HCID 86758100, compound → HCID 86756035, compound

Participants

Reaction Steps

cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-8-nitro-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 107) (0.747 g, 1.25 mmol), ethanol (20 mL), and 10% palladium on carbon (0.40 g) were combined and agitated under 36 psi of H2 on a Parr shaker for 2 h and 15 min. The mixture was then filtered through a bed of Celite®. The Celite® was washed with ethanol, and the filtrate was concentrated in vacuo. Purification by silica gel chromatography using 30-100% ethyl acetate/hexanes as eluent afforded 0.386 g (54%) of cis-8-amino-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-chloro-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester MS m/z 568 (M++H); 1H NMR (CDCl3) δ 7.8 (bs, 1H), 7.7 (bs, 1H), 7.65 (bs, 1H), 6.7 (bs, 1H), 6.38 (bs, 1H), 3.78 (s, 3H), and 0.161 g (24%) of cis-8-amino-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester MS m/z 534 (M++H); 1H NMR (CDCl3) δ 7.79 (bs, 1H), 7.7 (bs, 1H), 7.65 (bs, 1H), 7.02 (bt, 1H), 6.72 (bs, 1H), 6.4 (bd, 1H), 3.78 (s, 3H).

Provenance & Evidence