Hydrochloric Acid → 2-[2-[8-(4-chlorophenyl)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acid

HRID 1788608Notes

Reaction equation

HRID 1788608 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19](=O)[CH3:20])=[CH:10][C:11]3[O:17][CH2:16][CH2:15][CH2:14][O:13][C:12]=3[CH:18]=2)=[CH:4][CH:3]=1.C([O:24][C:25]([C:27]1[CH:50]=[CH:49][C:30]2[N:31]([CH:43]3[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]3)[C:32]([C:34]3[CH:39]=[CH:38][C:37]([NH2:40])=[C:36]([CH:41]=O)[CH:35]=3)=[N:33][C:29]=2[CH:28]=1)=[O:26])C.[OH-].[K+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:19]3[CH:20]=[CH:41][C:36]4[C:37](=[CH:38][CH:39]=[C:34]([C:32]5[N:31]([CH:43]6[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]6)[C:30]6[CH:49]=[CH:50][C:27]([C:25]([OH:26])=[O:24])=[CH:28][C:29]=6[N:33]=5)[CH:35]=4)[N:40]=3)=[CH:10][C:11]3[O:17][CH2:16][CH2:15][CH2:14][O:13][C:12]=3[CH:18]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 689242611-[8-(4-Chloro-phenyl)-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl]-ethanoneHCID 866003822-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

Product 1

HCID 52761502-[2-[8-(4-chlorophenyl)-3,4-dihydro-2H-1,5-benzodioxepin-7-yl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

1-[8-(4-Chloro-phenyl)-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl]-ethanone (76 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 132 mg of the title compound.

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-c81dd56e7d224caf9b58cfef39785b59
Source dataset
uspto-grants-2009_03
Patent number
US07511145B2

Reaction notes

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