Sodium Hydroxide → HCID 58926731, compound

Participants

Reaction Steps

Inject titanium(IV)isopropoxide (0.0870 ml, 0.299 mmol) to a mixture of 2-ethyl-7-methyl-4-oxo-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid isopropyl ester (0.055 g, 0.199 mmol), and 3,5-bis(trifluoromethyl)benzylamine (0.0500 g, 0.199 mmol), and then stir at room temperature for 6 h. Add methanol (2 ml) followed by NaBH4 (0.0380 g, 0.995 mmol) and stir at room temperature overnight. Treat the mixture with 1 N sodium hydroxide (2 ml) and ethyl acetate (5 ml), and then filter through a Celite® pad. Wash the filtered residue thoroughly with ethyl acetate (30 ml). Separate the organic layer, wash with brine (3×50 ml), dry over sodium sulfate, filter, and concentrate to provide crude 4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-7-methyl-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid isopropyl ester (0.0900 g) which was elaborated without further purification. MS (ES+): 504 (M+H).

Provenance & Evidence