Reaction Steps
To the crude product from the previous reaction, {6-[(methanesulfonyl)methyl]-3-[(isoquinoline-1-carbonyl)-amino]-2-oxo-2,3,4,7-tetrahydro-azepin-1-yl}-acetic acid methyl ester, 23, (0.147 g, 0.32 mmol) in CH2Cl2 (1 mL), is added benzylamine (1 mL). The reaction is stirred at room temperature for 10 minutes, then the reaction is diluted with CH2Cl2. The organic layer is washed with saturated NaHCO3, saturated NaCl, and dried (Na2SO4). The solvent is removed in vacuo and the resulting crude material is purified by HPLC to afford 82 mg (44% yield) of the desired product as the trifluoroacetate salt. 1H (CDCl3) δ 8.82–8.79 (d, J=6.1 Hz, 1H), 8.61–8.59 (d, J=8.6 Hz, 1H), 8.33–8.31, (d, J=5.8 Hz, 1H), 8.01–7.99 (d, J=5.94 Hz, 1H), 7.95–7.82 (m, 2H), 7.77–7.72 (d, d, J=7.98, 7.98 Hz, 1H), 7.36–7.18 (m, 5H), 5.91 (bs, 1H), 5.40–5.39 (m, 1H), 4.67–4.61 (d, J=17.4 Hz, 1H), 4.55–4.49 (d, J=17.8 Hz, 1H), 4.19–4.05 (m, 1H), 3.88–3.83 (d, J=14.7 Hz, 1H), 3.77–3.57 (m, 3H), 3.50 (s, 3H), 2.84–2.78 (d, J=17.8 Hz, 1H), 2.50–2.40 (d, d, J=15.8, 14.5 Hz, 1H); 13C (CDCl3) 171.9, 171.5, 161.9, 161.4, 160.9, 160.6, 149.1, 139.1, 135.2, 134.7, 134.2, 131.3, 130.3, 130.2, 130.1, 129.6, 128.2, 127.9, 127.8, 127.4, 125.8, 121.5, 117.7, 113.8, 110.0, 53.5, 52.9, 51.6, 49.8, 48.3, 37.9, 31.6; MS 473 (M+H)+.
