反应详情

1,1-Dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (Preparation 16) (505 mg, 1.064 mmol) was dissolved in DCM (40 ml) and treated with trifluoroacetic acid (4 ml, 51.9 mmol). The resulting mixture was heated at reflux for 1 hour then evaporated. The resulting residue was partitioned between DCM (20 ml) and 2N NaOH (20 ml). The DCM layer was collected, dried (hydrophobic frit) and evaporated. The free-base was dissolved in 4M HCl in dioxane and evaporated to give the HCl salt, 2-[(1-methylethyl)oxy]-5-[3-(2,3,4,5-tetrahydro-1H-3-benzazepin-6-yl)-1,2,4-oxadiazol-5-yl]benzonitrile hydrochloride (438 mg, 1.066 mmol, 100% yield) as an off-white powder. δH (400 MHz, CDCl3) 10.15 (1H, br.s), 8.39 (1H, s), 8.33-8.31 (1H, m), 7.75-7.85 (1H, m), 7.45-7.3 (2H, m), 7.14 (1H, d), 4.84-4.76 (1H, m), 3.90-3.30 (8H, m) 1.48 (6H, d); MS (ES) C22H22N4O2 requires 374; found 375 [M+H]+.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux for 1 hour
3. customthen evaporated
4. customThe resulting residue was partitioned between DCM (20 ml) and 2N NaOH (20 ml)
5. customThe DCM layer was collected
6. customdried (hydrophobic frit)
7. customevaporated
8. dissolutionThe free-base was dissolved in 4M HCl in dioxane
9. customevaporated