Sodium hydride → 2-[8-(Benzothiazol-2-ylcarbamoyl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-{3-[4-(4-cyano-thiophen-3-yl)-phenoxy]-propyl]-thiazole-4-carboxylic acid

Participants

Reaction Steps

To compound 51A (0.095 g, 0.015 mmol) in DMF (4 mL) was added 60% sodium hydride (0.036 g, 0.9 mmol) at 0° C. The solution was stirred for 10 minutes. To this solution was added compound 2C. The solution was stirred at rt for 2 hours. The reaction was quenched with MeOH (1 mL). Conc. HCl (0.5 mL) was added, and the solution was filtered through a syringe filter. The filtrate was then purified by Prep HPLC to provide the desired product 51: 1H NMR (DMSO-d6): δ 8.57 (d, J=3.38 Hz, 1H), 7.95 (d, J=7.98 Hz, 1H), 7.71-7.72 (m, 2H), 7.60 (d, J=7.36 Hz, 1H), 7.45-7.48 (m, 2H), 7.26-7.41 (m, 4H), 6.95-6.97 (m, 214), 4.77 (s, 2H), 3.97 (t, J=6.29 Hz, 2H), 3.66 (t, J=5.98 Hz, 2H), 3.11-3.14 (m, 2H), 2.96 (t, J=5.98 Hz, 2H), 1.93-2.00 (m, 2H); MS (ESI(+)): m/z 678 (M+H).

Provenance & Evidence