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

HRID 1788606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1788606
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]2[C:11]([C:12](=O)[CH3:13])=[CH:10][C:9]([N+:15]([O-])=O)=[CH:8][CH:7]=2)=[CH:4][CH:3]=1.C([O:22][C:23]([C:25]1[CH:48]=[CH:47][C:28]2[N:29]([CH:41]3[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]3)[C:30]([C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([CH:39]=O)[CH:33]=3)=[N:31][C:27]=2[CH:26]=1)=[O:24])C.[OH-].[K+].Cl>C(O)C>[NH2:15][C:9]1[CH:10]=[C:11]([C:12]2[CH:13]=[CH:39][C:34]3[C:35](=[CH:36][CH:37]=[C:32]([C:30]4[N:29]([CH:41]5[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]5)[C:28]5[CH:47]=[CH:48][C:25]([C:23]([OH:24])=[O:22])=[CH:26][C:27]=5[N:31]=4)[CH:33]=3)[N:38]=2)[C:6]([C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 860270631-(4'-Chloro-4-nitro-biphen-2-yl)-ethanoneHCID 866003822-(4-amino-3-formyl-phenyl)-1-cyclohexyl-1H-benzoimidazole-5-carboxylic acid ethyl ester

Produkt 1

HCID 52761542-[2-[5-Amino-2-(4-chlorophenyl)phenyl]-6-quinolyl]-1-cyclohexyl-benzimidazole-5-carboxylic acidAusbeute 12,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

1-(4′-Chloro-4-nitro-biphen-2-yl)-ethanone (69 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. for 3 days. 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 18 mg product.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-31f9c0f61d9249b9b6c327d0605ace27
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07511145B2

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