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HCID 18680797, Verbindung → HCID 18680884, Verbindung

HRID 1699631
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1699631
[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>[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 18680797HCID 18680797, VerbindungHCID 18680816HCID 18680816, Verbindung

Produkt 2

HCID 18680884HCID 18680884, VerbindungHCID 18681104HCID 18681104, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator
HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

Methanol (30 ml) and 5% palladium/carbon (0.20 g) are added to a mixture (2.32 g) of 2-methyl-1-(4-nitrobenzyl)-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 2-methyl-1-(4-nitrobenzyl)-5-[(2-pyridylmethyl)carbamoyl]benzimidazole, and the solution is stirred at room temperature under a nitrogen environment until the raw materials dissolved. Solid materials are separated through filtration. The filtrate is concentrated and a residue is obtained. The residue is purified through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=85/15), and 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole are separated. These materials are crystallized in mixed solvents of chloroform and diethylether. The crystals are separated through filtration, dried and thus, 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole (0.354 g) (197) and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole (0.330 g) (198) are obtained. 1H-NMR (CDCl3, δ): 3.00 (3H, s), 4.98 (2H, s), 5.88 (2H, s), 7.55 (2H, d, J=8.6 Hz), 7.69 (2H, d, J=8.6 Hz), 7.90 (1H, d, J=8.6 Hz), 7.96 (1H, dt, J=7.1 and 0.6 Hz), 8.12 (1H, J=8.0 Hz), 8.18 (1H, dd, J=8.5 and 1.4 Hz), 8.55 (1H, dt, J=8.0 and 1.7 Hz), 8.62 (1H, d,J=1.1 Hz), 8.77(1H, dd, J=5.9 and 1.1 Hz).

Aufarbeitung

  1. dissolutiondissolved
  2. customSolid materials are separated through filtration
  3. concentrationThe filtrate is concentrated
  4. customa residue is obtained
  5. customThe residue is purified through medium pressure silica gel column chromatography (eluate: ethyl acetate/methanol=85/15), and 1-(4-aminobenzyl)-2-methyl-6-[(2-pyridylmethyl)carbamoyl]benzimidazole and 1-(4-aminobenzyl)-2-methyl-5-[(2-pyridylmethyl)carbamoyl]benzimidazole
  6. customare separated
  7. customThese materials are crystallized in mixed solvents of chloroform and diethylether
  8. customThe crystals are separated through filtration
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-333b11ea43374cde9b1eb571c4808fcd
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06348032B1

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