3-Phenylpropylamine → N-(3-Phenylpropyl) 3-(4-Cyanophenyl)-2,3-dihydro-imidazo[2,1-b]thiazole-5-carboxamide hydrochloride

Participants

Reaction Steps

The carboxylic acid from Step D, Example 1 (20.0 mg, 0.0625 mmol), 3-phenylpropylamine (0.0089 mL, 0.0625 mmol), EDC hydrochloride (14.4 mg, 0.0751 mmol), HOBT (10.1 mg, 0.0751 mmol), and N,N-diisopropylethylamine (0.044 mL, 0.250 mmol) were stirred in dry, degassed DMF (1 mL) at 25° C. for 16 hours. The crude product was purified by preparative HPLC using a gradient of 5%-95% acetonitrile/0.1% TFA; 95%-5%/0.1% aqueous TFA over 15 min. The title compound was isolated after conversion to the HCl salt. MS (es) m+1=389. 1H-NMR (CD3OD): δ7.72 (d, 2H, J=8.2 Hz); 7.71 (s, IH); 7.24 (d, 2H, J=8.2 Hz); 7.23 (t, 2H, J=7.9 Hz); 7.14 (t, 1H, J=7.6 Hz); 7.10 (d, 2H, J=7.3 Hz); 6.38 (bd, 1H, J=7.4 Hz); 4.70 (dd, 1H, J=11.6, 8.4 Hz); 3.81 (d, 1H, J=11.6 Hz); 3.14-3.22 (m, 2H); 2.53 (t, 2H, J=7.7 Hz), 1.73-1.80 (m, 2H).

Provenance & Evidence