Fasudil → 5-({1-[(2R)-2-propyloctanoyl]azepan-4-yl}sulfonyl)quinoline

Participants

Reaction Steps

(R)-2-propyloctanoic acid (100 mg, 0.48 mmol) was dissolved in 1 mL DMF. HATU (201 mg, 0.53 mmol) and NMM (64 μL, 0.58 mmol) were added and the solution was stirred for 5 min. Fasudil (154 mg, 0.53 mmol) was added and the solution was stirred for 2 h at rt. The reaction was quenched with TFA (48 μL, 0.63 mmol) and MeOH (1 mL) and purified by preparative HPLC (50% to 100% ACN/water) to give the product (Example 5) as a white solid. 1H-NMR (500 MHz, CDCl3) δ 9.81 (s, 1H), 8.94 (d, 1H), 8.70 (d, 1H), 8.54-8.60 (m, 2H), 7.98 (t, 1H), 7.28 (s, 1H), 3.71-3.76 (m, 4H), 3.45-3.48 (m, 4H), 2.56-2.58 (m, 1H), 2.04-2.07 (m, 2H), 1.59-1.65 (m, 2H), 1.43-1.44 (m, 2H), 1.26-1.29 (m, 10H), 0.86-0.91 (m, 6H). MS (ESI) 460 (M+H).

Provenance & Evidence