Ammonium Chloride → HCID 86759968, compound

Participants

Reaction Steps

A mixture of (1S)-(2-amino-1-[2-trifluoromethyl]-1,3-thiazole-4-yl]ethanol (which was obtained in Example 105) (0.34 g, 1.59 mmol) and 5-[4-(4-oxopiperidine-1-yl)benzyl]-1,3-thiazolidine-2,4-dione (which was obtained in Example 38) (0.48 g, 1.59 mmol), sodium triacetoxyborohydride (0.67 g, 3.18 mmol), and acetic acid (0.33 mL) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 18 hours, poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic extracts were washed with brine and dried over MgSO4. Evaporation and purification by flash chromatography (chloroform/methyl alcohol 9.5/5) gave a yellow solid (0.1 g, 13% yield); mp 108–113° C.; MS (ES) m/z: 501 (MH+); 1H NMR (400 MHz, DMSO-d6) δ 1.44 (m, 2H), 1.93 (s, 2H), 3.23–2.66 (m, 7H), 3.62 (d, 2H) 4.68 (m, 1H), 4.94 (m, 1H), 6.86 (d, 2H), 7.5 (d, 2H), 8.3 (s, 1H); Anal. Calcd. for C21H23F3N4O3S2: C, 50.39; H, 4.63; N, 11.19. Found: C, 50.16; H, 5.16; N, 9.93.

Provenance & Evidence