Hydrochloric Acid → 5-{4-[4-((2s)-2-Hydroxy-3-phenoxy-propylamino)-piperidin-1-yl]-benzylidene}-2-morpholin-4-yl-thiazol-4-one dihydrochloride salt

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Reaction Steps

The free base was prepared from 1-[4-(2-morpholin-4-yl-4-oxo-4H-thiazol-5-ylidenemethyl)-phenyl]-piperidin-4-one (which was obtained in Intermediate 28) and (2S)-1-amino-3-phenoxy-propan-2-ol (which was obtained in Intermediate 3) according to the procedure of Example 1. The free base was dissolved in methanol/dichloromethane and treated with hydrogen chloride gas. After concentrated the solvents the product was obtained as a yellowish solid; mp>160° C. (dec.); 1H NMR (300 MHz, DMSO-d6) δ1.60-1.90 (m, 2 H), 2.05-2.25 (m, 2 H), 2.80-3.30 (m, 7 H), 3.60-4.40 (m, 11 H), 6.90-7.10(m, 3 H), 7.14(d, J=8.7 Hz, 2 H), 7.51 (d, J=8.7 Hz, 2 H), 7.57 (s, 1 H), 8.92(brs, 1 H), 9.36(brs, 1 H); MS (ES) m/z: 262.1 ((M+2H)2+, 100%); 523.1(MH+, 30%); HRMS Calcd. for C28H35N4O3S (MH+): 523.2379 Found: 523.2394.

Provenance & Evidence