Potassium Carbonate → 1-Ethyl-3,3,5-trimethyl-7-[3-(2-phenyl-benzoimidazol-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hydrochloride

HRID 69056

Reaction equation

HRID 69056 reaction equation
[C:1]1([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([N:24]1[C:30](=[O:31])[C:29]([CH3:33])([CH3:32])[C:28](=[O:34])[N:27]([CH3:35])[C:26]2[CH:36]=[C:37]([O:40][CH2:41][CH2:42][CH2:43]I)[CH:38]=[CH:39][C:25]1=2)[CH3:23].C(O)C.[ClH:48]>C(O)(C)C.CN(C=O)C>[ClH:48].[CH2:22]([N:24]1[C:30](=[O:31])[C:29]([CH3:32])([CH3:33])[C:28](=[O:34])[N:27]([CH3:35])[C:26]2[CH:36]=[C:37]([O:40][CH2:41][CH2:42][CH2:43][N:11]3[C:10]4[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=4[N:8]=[C:7]3[C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:38]=[CH:39][C:25]1=2)[CH3:23]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 128552-PhenylbenzimidazoleHCID 21887872Ethanol hydrochlorideHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 706566741-Ethyl-3,3,5-trimethyl-7-[3-(2-phenyl-benzoimidazol-1-yl)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione hydrochloride

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Phenyl-1H-benzimidazole (0.2 g) and potassium carbonate (0.29 g) were added to a DMF solution (5 ml) of 1-ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.49 g). The mixture was stirred at 60° C. for 7 hours. The reaction mixture was poured to ice water (50 ml), and the generated insoluble matter was separated. The insoluble matter was dissolved in ethyl acetate. The liquid was dried over sodium sulfate and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride ethanol solution (1.0 ml) was added to an isopropyl alcohol solution of the residue. The mixture was condensed under reduced pressure. Ether was added to the residue. The generated insoluble matter was separated by filtration and dried to give the title compound (0.32 g) as a white powder.

Workup

  1. customthe generated insoluble matter was separated
  2. dissolutionThe insoluble matter was dissolved in ethyl acetate
  3. dry with materialThe liquid was dried over sodium sulfate and condensed under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:3)
  5. customcondensed under reduced pressure
  6. customcondensed under reduced pressure
  7. customThe generated insoluble matter was separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-de8ab4288e134fb39d21852ded4f2ecc
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Linked notes

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