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HCID 18680797, Verbindung → HCID 18680884, Verbindung

HRID 276060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276060
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)[C:5]2[CH:17]=[C:18]([C:21](=[O:30])[NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)[CH:19]=[CH:20][C:4]=2[N:3]=1.[CH3:31][C:32]1[N:36]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([N+:44]([O-])=O)=[CH:40][CH:39]=2)[C:35]2[CH:47]=[CH:48][C:49]([C:51](=[O:60])[NH:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=3)=[CH:50][C:34]=2[N:33]=1.[H][H]>[Pd].CO>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][N:6]2[C:5]3[CH:17]=[C:18]([C:21](=[O:30])[NH:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:19]=[CH:20][C:4]=3[N:3]=[C:2]2[CH3:1])=[CH:13][CH:12]=1.[NH2:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][N:36]2[C:35]3[CH:47]=[CH:48][C:49]([C:51](=[O:60])[NH:52][CH2:53][C:54]4[CH:59]=[CH:58][CH:57]=[CH:56][N:55]=4)=[CH:50][C:34]=3[N:33]=[C:32]2[CH3:31])=[CH:43][CH:42]=1
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Komponenten

7

Edukt 3

HCID 18680797HCID 18680797, VerbindungHCID 18680816HCID 18680816, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 2

HCID 18680884HCID 18680884, VerbindungHCID 18681104HCID 18681104, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

Thirty milliliters of methanol and 0.20 g of 5% palladium on carbon were added to 2.32 g of a mixture of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]-benzimidazole, and the mixture was stirred in a hydrogen atmosphere at room temperature until the starting material disappeared. The solid material was separated through filtration, and the filtrate was concentrated. The resulting residue was purified through medium-pressure silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 85:15) to separate 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole. Each of these compounds was crystallized from a mixed solvent of chloroform and diethyl ether. The crystals were separated through filtration, and were dried to give 0.354 g of 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]-benzimidazole (261) and 0.330 g of 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (262).

Aufarbeitung

  1. customThe solid material was separated through filtration
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified through medium-pressure silica-gel column chromatography (eluent
  4. additiona mixture of ethyl acetate and methanol at a ratio of 85:15)
  5. customto separate 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole
  6. customEach of these compounds was crystallized from a mixed solvent of chloroform and diethyl ether
  7. customThe crystals were separated through filtration
  8. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-5ea1a25466364882b0733af1fca31599
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352985B1

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