1,3,4-Thiadiazol-2-amine → N-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropyl)-1,3,4-thiadiazol-2-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal (419 mg, 1.12 mmol) in ClCH2CH2Cl (20 mL) was added 1,3,4-thiadiazol-2-amine (137 mg, 1.35 mmol) and titanium tetraisopropoxide (0.35 mL, 1.2 mmol) at RT under nitrogen. The reaction mixture was heated at 85° C. for 1 hr then sodium triacetoxyborohydride (318 mg, 1.5 mmol) was added and the reaction was heated at 85° C. for 4 hr. The reaction mixture was poured into a sat. sodium bicarbonate solution (100 mL), extracted with CH2Cl2 (100 mL), dried (Na2SO4) and concentrated. The final product was purified using HPLC to give 95 mg (19% yield) of N-(3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropyl)-1,3,4-thiadiazol-2-amine which showed consistent 1H-NMR spectra. MS found: (M+H)+=458. NMR (CDCl3) δ 11.3 (bs, 1H); 8.12 (s, 1H); 8.03 (s, 1H); 7.82 (s, 1H); 7.52-7.55 (m, 2H); 7.48 (s, 1H); 7.39-7.41 (d, 2H); 7.11-7.23 (m, 5H); 4.16 (s, 1H), 3.09-3.18 (q, 2H); 1.18 (s, 6H).

Provenance & Evidence