Diazepam → HCID 67514039, compound

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 6-[4-(chlorocarbonyl)-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1H-benzimidazole-1-carboxylate (5.5 mg, 16 μmol) and 2-(piperazin-1-yl)pyrimidine (7.9 mg, 48 μmol) in anhydrous DCM (2 mL) was added PL-DIPAM (85 mg, 3.27 mmol/g loading, 315 μmol, Polymer Labs) and the reaction mixture was shaken overnight at room temperature. The resulting mixture was drained into PL-PETA (55 mg, 2.7 mmol/g loading, 175 μmol, Polymer Labs) and PL-MIA, (35 mg, 2.65 mmol/g loading, 104 μmol, Polymer Labs). The reaction mixture was shaken overnight at room temperature, drained and the resin was washed with 3.0 mL of methanol. The combined methanol solution was transferred to a 2 dram vial and concentrated under reduced pressure. The resulting oil was dissolved in methanol (2 mL) followed by the addition of 4 N anhydrous hydrogen chloride in dioxane (0.5 mL, Aldrich). The mixture was shaken at room temperature for an additional 18 hours. The resulting solution was concentrated under reduced pressure to give 7-(2-methyl-1H-benzimidazol-6-yl)-4-[(4-pyrimidin-2-ylpiperazin-1-yl)carbonyl]-2,3,4,5-tetrahydro-1,4-benzoxazepine. MS (EI) for C26H27N7O2: 470.5 (MH+).

Provenance & Evidence