Hydrochloric Acid → 1-Cyclohexyl-2-[2-(2-ethoxy-5-nitro-phenyl)-6-quinolyl]benzimidazole-5-carboxylic acid

HRID 1788581Notes

Reaction equation

HRID 1788581 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11](=O)[CH3:12].C([O:16][C:17]([C:19]1[CH:42]=[CH:41][C:22]2[N:23]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:24]([C:26]3[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([CH:33]=O)[CH:27]=3)=[N:25][C:21]=2[CH:20]=1)=[O:18])C.[OH-].[K+].Cl.[CH2:46]([OH:48])[CH3:47]>>[CH:35]1([N:23]2[C:22]3[CH:41]=[CH:42][C:19]([C:17]([OH:16])=[O:18])=[CH:20][C:21]=3[N:25]=[C:24]2[C:26]2[CH:27]=[C:28]3[C:29](=[CH:30][CH:31]=2)[N:32]=[C:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[O:48][CH2:46][CH3:47])[CH:12]=[CH:33]3)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 234021201-(2-Bromo-5-nitrophenyl)ethanoneHCID 866003822-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

Product 1

HCID 52760251-Cyclohexyl-2-[2-(2-ethoxy-5-nitro-phenyl)-6-quinolyl]benzimidazole-5-carboxylic acid

Conditions

Temperature
75 °C

Procedure

1-(2-Bromo-5-nitro-phenyl)-ethanone (61 mg, 0.25 mmol) prepared similarly to the procedure described in Meisenheimer, J., Zimmermann P., and v. Kummer, U. Ann. der. Chem. 446, pp. 205-228) and 2-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester (98 mg, 0.25 mmol) were dissolved in 500 μL ethanol and 500 μL 10% ethanolic KOH were added. The reaction was stirred at 75° C. overnight. The reaction was acidified with 4N hydrochloric acid, extracted three times with ethyl acetate, the organic extracts were dried with sodium sulfate and then evaporated. Purification via reverse-phase HPLC gave 16 mg (97.33% pure) of product.

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialthe organic extracts were dried with sodium sulfate
  3. customevaporated
  4. customPurification via reverse-phase HPLC
  5. customgave 16 mg (97.33% pure) of product

Sources & evidence

ORD record
ord-5db50e0236924a6abcb3d528a899adb3
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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