Ammonium Chloride → HCID 86753594, compound

Participants

Reaction Steps

To a stirring solution of 2.33 g (4.93 mmol) of 2-(3-Methyl-2,4-dioxo-5-pyridin-3-yl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-(4-methoxy-phenyl)-acetamide, prepared as in Part A, in 50 mL of DMF at 0° C. is added 5.42 mL (5.42 mmol) of a 1.0M solution of NaN(TMS)2 in THF. The resulting solution is stirred 10 min, then a solution of 1.69 g (5.42 mmol) of 3-bromomethyl-1-tert-butoxycarbonyl-1H-indazole in 10 mL of DMF is added. The resulting solution is stirred at RT for 2 h then poured into 100 mL NH4Cl. The reaction mixture is concentrated to remove the DMF, diluted with 300 mL of H2O and extracted with EtOAc (3×200 mL). The organics were dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash chromatography using hexane/EtOAc 3/1 as eluent afforded 2.41 g of the title compound as a light yellow foam: 1H NMR (CDCl3, 400 MHz) δ8.53 (m, 2H), 8.06 (m, 2H), 7.50-6.96 (m, 12H), 5.03 (m,1H), 4.58 (d, 1H), 4.06 (d, 1H), 3.85 (s, 3H), 3.02 (dd, AB quartet, 2H, J=16.8), 1.72 (s, 9H), 1.55 (s, 3H), 1.14 (d, 6H, J=6.8); low resolution MS (FAB)m/e 703 (MH+), 603, 438; Anal. (C40H42N6O6) Calcd. C, 68.36; H, 6.02; N, 11.96 Found C, 67.11; H, 6.15; N, 11.48.

Provenance & Evidence