Methanol → 2-[({1-[(3,5-Dichloro-2-hydroxyphenyl)methyl]4-fluoro-4-piperidyl}methyl)amino]benzimidazole-5-carboxylic acid methyl ester

HRID 2112551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2112551
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[CH:5]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[CH3:27][O:28][C:29]([C:31]1[CH:48]=[CH:47][C:34]2[N:35]=[C:36]([NH:38][CH2:39][C:40]3([F:46])[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[NH:37][C:33]=2[CH:32]=1)=[O:30].CO>CN(C=O)C.C(O)(=O)C>[CH3:27][O:28][C:29]([C:31]1[CH:48]=[CH:47][C:34]2[N:35]=[C:36]([NH:38][CH2:39][C:40]3([F:46])[CH2:45][CH2:44][N:43]([CH2:5][C:4]4[CH:7]=[C:8]([Cl:10])[CH:9]=[C:2]([Cl:1])[C:3]=4[OH:11])[CH2:42][CH2:41]3)[NH:37][C:33]=2[CH:32]=1)=[O:30]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 666603,5-DichlorosalicylaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 690664572-{[(4-Fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride

Produkt 1

HCID 102174892-[({1-[(3,5-Dichloro-2-hydroxyphenyl)methyl]4-fluoro-4-piperidyl}methyl)amino]benzimidazole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21926011acetic acid N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

After adding 3,5-dichloro-2-hydroxybenzaldehyde (57.3 mg, 0.3 mmol) and sodium triacetoxyborohydride (64 mg, 0.3 mmol) to a solution of 2-{[(4-fluoro-4-piperidyl)methyl]amino}benzimidazole-5-carboxylic acid methyl ester hydrochloride (30 mg, 0.1 mmol) in DMF-acetic acid (10:1) (1.0 ml), the mixture was stirred at room temperature overnight. Methanol (1.0 ml) was added to the reaction mixture to suspend the reaction, and after stirring for 1 hour, the solution was passed through SCX (Bond Elute SCX500MG: cationic ion-exchange resin, Varian). The SCX was washed with methanol and then with a mixed solution of chloroform/methanol (1/1), and elution was performed with a 0.5 N ammonia-dioxane solution to obtain 2-[({1-[(3,5-dichloro-2-hydroxyphenyl)methyl]4-fluoro-4-piperidyl}methyl)amino]benzimidazole-5-carboxylic acid methyl ester. The compound was identified by LC-MS.

Aufarbeitung

  1. customthe reaction
  2. stirringafter stirring for 1 hour
  3. washthe solution was passed through SCX (Bond Elute SCX500MG: cationic ion-exchange resin, Varian)
  4. washThe SCX was washed with methanol
  5. washwith a mixed solution of chloroform/methanol (1/1), and elution

Quellen und Nachweise

ORD-Eintrag
ord-8bc6c1ec95984e0daa3296e537a5c79d
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07524841B2

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