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Hydrochloric Acid → 2-[2-[2-(4-Chlorophenyl)-5-fluoro-phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788605
Notes
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Reaction equation

HRID 1788605 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[C:11]([C:12](=O)[CH3:13])=[CH:10][C:9]([F:15])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.C([O:20][C:21]([C:23]1[CH:46]=[CH:45][C:26]2[N:27]([CH:39]3[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]3)[C:28]([C:30]3[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([CH:37]=O)[CH:31]=3)=[N:29][C:25]=2[CH:24]=1)=[O:22])C.[OH-].[K+].Cl>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]2[C:11]([C:12]3[CH:13]=[CH:37][C:32]4[C:33](=[CH:34][CH:35]=[C:30]([C:28]5[N:27]([CH:39]6[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]6)[C:26]6[CH:45]=[CH:46][C:23]([C:21]([OH:22])=[O:20])=[CH:24][C:25]=6[N:29]=5)[CH:31]=4)[N:36]=3)=[CH:10][C:9]([F:15])=[CH:8][CH:7]=2)=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 860272381-(4'-Chloro-4-fluoro-biphen-2-yl)-ethanoneHCID 866003822-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

Product 1

HCID 52761482-[2-[2-(4-Chlorophenyl)-5-fluoro-phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid
Yield 58.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

1-(4′-Chloro-4-fluoro-biphen-2-yl)-ethanone (62 mg, 0.25 mmol) 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 84 mg 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

Sources & evidence

ORD record
ord-8352f928c7e34d6bb53ce46f2706993e
Source dataset
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07511145B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes