Hydrochloric Acid → HCID 22000406, compound

Participants

Reaction Steps

To a stirred solution of N1-{4-[(4,5-dihydro-benzo[2,3]oxepino[4,5-d][1,3]thiazol-2-ylamino)-methyl]cyclohexyl}acetamide (0.380 g, 1.02 mmol) in anhydrous THF (4 ml) was added 1M BH3 in THF (5.0 ml, 5.0 mmol). The solution was stirred at room temperature overnight. 4N HCl (12 ml) was added slowly and stirring continued for 15 minutes. The resulting solution was made basic (pH˜9) with 2N NaOH. The cloudy solution was extracted with EtOAc and the organic layer washed with water. Removal of the solvent in vacuo, gave 69% (252 mg) of the product as a solid which was used without further purification: 1H-NMR (CDCl3) δ 0.96 (4H, m), 1.08 (3H, t, J=7.1 Hz), 1.47 (1H, m), 1.76 (2H, d, J=12.1 Hz), 1.90 (2H, m), 2.37 (2H, m), 2.63 (2H, q, J=7.0 Hz), 3.05 (2H, t, J=5.7 Hz), 3.11 (2H, t, J=5.1 Hz), 4.28 (2H, t, J=5.2 Hz), 5.73 (1H, broad t), 6.96 (1H, dd, J=0.9 Hz, 7.7 Hz), 7.10 (2H, m), 8.22 (1H, dd, J=1.3 Hz, 7.6 Hz); 358 (ESMS, MH+).

Provenance & Evidence