Hydrochloric Acid → HCID 22000429, compound

Participants

Reaction Steps

To a stirred solution of N1-{4-[(4,5-dihydrobenzo[2,3]oxepino[4,5-d][1,3]thiazol-2- ylamino)-methyl]cyclohexyl}-2-methoxyacetamide (free-base) (0.450 g, 1.12 mmol) in anhydrous THF (5 ml) was added 5.0 ml 1M BH3 in THF (5.0 mmol). The solution was stirred at room temperature for 26 hours. 4N HCl (12 ml) was slowly added to the stirred solution and stirred continued for 1 hour. The solution was made basic with 2N NaOH (pH˜9) and was extracted with EtOAc. Upon evaporation of the solvent, 90% (390 mg) of the desired amine was obtained as a highly viscous colorless oil. The compound was converted to its dihydrochloride salt in chloroform with 1N HCl in Et2O. Evaporation of the solvent gave 460 mg of the salt as a slightly hygroscopic white solid: m.p. 243-245° C. (dec); 1H-NMR (CDCl3) δ 1.08 (4H, t, J=10.8 Hz), 1.6 (2H, broad), 1.91 (4H, m), 2.41 (1H, broad), 2.80 (2H, t, J=4.9 Hz), 3.15 (4H, m), 3.35 (3H, s), 3.49 (2H, t, J=5.3 Hz), 4.32 (2H, t, J=5.4 Hz), 5.13 (1H, broad t), 6.98 (1H, dd, J=1.3 Hz, 7.7 Hz), 7.12 (2H, m), 8.24 (1H, dd, J=1.6 Hz, 7.9 Hz); 388 (ESMS, MH+).

Provenance & Evidence