Phenethylamine → HCID 59129008, compound

Participants

Reaction Steps

A mixture of N-benzylmethylamine (68 μL, 0.53 mmol), diisopropylethylamine (187 μL, 1.06 mmol) and chloroacetamidine hydrochloride (68 mg, 0.53 mmol) in DMF (5 mL) was stirred at rt for 18 h. 2-(2-tert-butylphenoxy)-3-isothiocyanatopyridine (Example 1a) (150 mg, 0.53 mmol) was then added and mixture was stirred for 3 h at 80° C. The reaction mixture was cooled to rt and diethylazodicarboxylate (168 μL, 1.06 mmol) was added and mixture was stirred for 2 h. The reaction mixture was purified by preparative HPLC to give Example 94 (2 mg, 2TFA salt) as a white. (M+H)+=460. 1H NMR (400 MHz, DMSO d6) δ ppm 1.30 (s, 9 H), 2.26 (s, 3H), 3.64 (s, 2H), 3.67 (s, 2H), 6.92 (dd, J=7.83, 1.26 Hz, 1H), 7.12-7.39 (m, 9 H), 7.42 (dd, J=7.83, 1.52, 1H), 7.76 (dd, J=5.05, 1.26, 1H), 8.89 (d, J=7.58 Hz, 1H), 10.82 (s, 1 H).

Provenance & Evidence