Water → HCID 67210421, compound

Participants

Reaction Steps

[step 1] (E)-2-[8-(4-Methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetic acid (300 mg, 0.68 mmol) obtained in Example 105, step 1 was dissolved in THF (6.8 mL) and dichloromethane (6 mL), N,N′-carbonyldiimidazole (444 mg, 2.74 mmol) was added, and the mixture was stirred at room temperature for 4 hr. To the mixture was added hydrazine monohydrate (0.33 mL, 6.84 mmol), and the mixture was stirred at room temperature for 5 hr. Water was added to the mixture, and the mixture was extracted with chloroform (70 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 85/15) to give (E)-2-[8-(4-methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetohydrazide (309 mg, 100%). [step 2] (E)-2-[8-(4-Methyl-2-propylbenzimidazol-1-yl)methyl-6,11-dihydrodibenzo[b,e]oxepin-11-ylidene]acetohydrazide (118 mg, 0.25 mmol) obtained in step 1 was dissolved in dichloromethane (2.5 mL), N,N′-carbonyldiimidazole (120 mg, 0.74 mmol) was added, and the mixture was stirred at room temperature for 3 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate (80 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 93/7) to give the title compound (compound 106) (30 mg, 25%).

Provenance & Evidence