Reaction Steps
To a solution of {6-(aminomethyl)-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 29, (0.14 g, 0.37 mmol) in THF(1 mL) is added benzoyl chloride (80 μl, 0.75 mmol) and triethyl amine (0.71 mL, 4.99 mmol). The reaction is complete with a few minutes. Methanol (5 mL) is added to the reaction mixture and then the solvents are removed in vacuo to provide a residue which is purified by HPLC to afford 84 mg (46% yield) of the desired product. 1H NMR (CDCl3) δ 9.37–9.33 (d, J=9.4 Hz, 1H), 9.06–9.03 (d, J=5.5 Hz, 1H), 7.73–7.64 (m, 4H), 7.59–7.48 (m, 2H), 7.41–7.48 (m, 4H), 5.68 (bs, 1H), 5.37–5.30 (m, 1H), 4.644.57 (d, d, J=17.5, 2.37 Hz, 1H), 4.4.6–4.40 (d, J=17.6 Hz, 1H), 4.15–4.08 (d, d, J=14.5, 6.9 Hz, 1H), 3.82–3.76 (d, J=17.6 Hz, 1H), 3.76–3.70 (d, d, J=14.7 Hz, 1H), 3.42 (s, 3H), 3.38–3.33 (d, J=17.6 Hz, 1H), 2.81–2.76 (m, 1H), 2.35–2.25 (d, d, J=16.3, 14.2 Hz, 1H); 13C (CDCl3) 172.6, 170.5, 168.0, 165.9, 148.2, 141.0, 137.7, 134.3, 133.8, 132.4, 132.3, 132.0, 130.7, 129.0, 128.9, 127.7, 127.6, 127.5, 127.2, 124.7, 52.6, 50.5, 49.3, 49.1, 46.7, 32.6; MS 487 (M+H).
