Methyl iodide → HCID 67696539, compound

Participants

Reaction Steps

To a stirring solution of 2.65 g (5.78 mmol) of 2-(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 in 80 mL of DMF at 0° C. is added 6.36 mL (6.36 mmol) of a 1.0M solution of NaN(TMS)2 in THF. The resulting solution is stirred 10 min, then 400 mL (6.36 mmol) of methyl iodide is added neat. The resulting solution is stirred at RT for 45 min then poured into 100 mL NH4Cl. The reaction mixture is concentrated to remove the DMF, diluted with 500 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 EtOAc as eluent afforded 2.52 g 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 as a white foam: 1H NMR (CDCl3, 400 MHz) δ8.50 (s, br, 2H), 7.79 (d, 1H, J=8.1), 7.43 (d, 1H, J=8.1), 7.36-6.94 (m, 8H), 6.88 (d, 1H, J=8.8), 4.98 (m, 1H), 4.26 (m, 2H), 3.85 (s, 3H), 3.54 (q, 1H, J=7.1), 1.42 (d, 3H, J=7.1), 1.07 (m, 6H); low resolution MS (FAB)m/e 473 (MH+); Anal. (C27H28N4O4) Calcd. C, 68.63; H, 5.97; N, 11.86 Found C, 66.91; H, 6.13; N, 11.29.

Provenance & Evidence