Water → HCID 67210421, compound

HRID 452164Notes

Reaction equation

HRID 452164 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:33]=[CH:32][C:18]4/[C:19](=[CH:28]\[C:29](O)=O)/[C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5O[CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH2:34].[NH2:35][NH2:36].[OH2:37]>C1COCC1.ClCCl>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:33]=[CH:32][C:18]4/[C:19](=[CH:28]\[C:29]([NH:35][NH2:36])=[O:37])/[C:20]5[CH:21]=[CH:24][CH:25]=[CH:26][C:27]=5[O:34][CH2:23][C:17]=4[CH:16]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 67210490HCID 67210490, compound

Product 1

HCID 67210421HCID 67210421, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

[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%).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionthe mixture was extracted with chloroform (70 mL)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 85/15)

Sources & evidence

ORD record
ord-54b44bc24508461287408d2a9018e607
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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