Imidazole → 4-(Benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one

4-(Benzyloxycarbonyl)-1-(2-hydroxyethyl)-piperazin-2-one, prepared as described in EXAMPLE 94, part A. (0.26 g, 0.94 mmol) in methylene chloride (6 mL) is treated with triphenyl phosphine (0.60 g, 2.3 mmol), imidazole (0.16 g, 2.3 mmol), and iodine (0.47 g, 1.9 mmol) for 0.5 h at 0° C. The reactin mixture is partitioned between water and methylene chloride; the organic layer is concentrated and the residue is chromatographed (15% EtOAc/methylene chloride) to give 4-(benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one (0.24 g, 0.62 mmol). Pyrrolo[3,2-c]pyridine (0.073 g, g, 0.62 mmol) is dissolved in DMF (3 mL) and treated with 60% sodium hydride (0.03 g, 0.74 mmol) and all of the 4-(benzyloxycarbonyl)-1-(2-iodoethyl)-piperazin-2-one from the previous step; the reaction mixture is stirred at r.t. for 16 g. The reaction mixture is concentrated to dryness and the residue is partitioned between water and methylene chloride. The organic layer is concentrated and subjected to chromatography (2-5% MeOH/methylene chloride) to yield the title compound (0.028 g, 0.074 mmol) Ion Spray MS m/z: 379, [M+1]+.

1. customThe reactin mixture is partitioned between water and methylene chloride
2. concentrationthe organic layer is concentrated
3. customthe residue is chromatographed (15% EtOAc/methylene chloride)

ORD record

ord-51b8a970de644ba584173c9330b71da4

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07612075B2