Hydrochloric Acid → HCID 57135628, compound

Participants

Reaction Steps

The fourth material to elute from the column of Example 48 (870 mg, 1.57 mmol) was deprotected with tetraethylammonium fluoride hydrate as in Example 44. Chromatography over silica gel with acetonitrile gave an off-white glass. 1H-NMR (300 MHz, DMSO-d6): δ 0.90 (d, J=6.0 Hz, 3H); 1.07 (t, J=7.0 Hz, 6H); 1.15 (d, J=5.7 Hz, 3H) 1.74 (m, 1H); 1.97 (m, 1H); 2.35 (m, 2H); 2.60-2.80 (m, 3H); 3.30 (m, 5H); 5.15 (m, 2H); 5.29 (s, 1H); 5.80 (m, 1H); 6.66 (s, 1H); 6.73 (s, 1H); 6.74 (d, J=7.5 Hz, 2H); 7.19 (t, J=7.5 Hz, 1H); 7.56 (s, 1H); 9.45 (s, 1H). The amine was dissolved in ethanol and converted to the monohydrochloride salt by titration to pH 3.8 with ethanolic hydrochloric acid. The solvent was removed by evaporation and the salt was dissolved in dichloromethane, followed by precipitation with diethyl ether to give 280 mg (37%) of a white solid, mp 109°-116° C. Calculated for C25 H35N3O2S HCl 0.5 H2O: C, 61.65; H, 7.66; N, 8.63; Cl, 7.28; S, 6.58. Found: C, 61.58; H, 7.65; N, 8.54; Cl, 7.36; S, 6.53.

Provenance & Evidence