Dichloromethane → 1-{5-[5-(4-Isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethanamine

Participants

Reaction Conditions

Reaction Steps

A solution of Example 24F (0.48 g, 0.98 mmol) in CH2Cl2/ethanol (1:1, v/v, 12 mL) was treated with hydrazine hydrate (0.476 mL, 9.79 mmol). The reaction was stirred at 25° C. for 5 hours and was concentrated under reduced pressure on a rotary evaporator to provide a residual oil. The concentrate was treated with CH2Cl2 (15 mL) and a white suspension formed. The suspension was filtered and the filtrate was concentrated on a rotary evaporator to provide 0.32 g of a pale yellow oil. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 98:1:1 to 97:2:1 CH2Cl2/CH3OH/NH4OH to provide 0.09 g (25%) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.46 (d, J=3.68 Hz, 1H) 7.38 (d, J=9.19 Hz, 2H) 7.02 (d, J=9.19 Hz, 2H) 6.96 (dd, J=3.68, 0.74 Hz, 1H) 4.63 (heptet, J=5.88 Hz, 1H) 4.17-4.29 (m, 1H) 1.35 (d, J=6.62 Hz, 3H) 1.28 (d, J=5.88 Hz, 6H); MS (APCI) m/z 362 (M+H)+.

Provenance & Evidence