Potassium Carbonate → 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrrole

HRID 1871124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871124
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([O:11][CH3:12])[N:7](C)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:14]([NH:17][C:18]1[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][C:30]2[N:31]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH2:42]OS(C)(=O)=O)[C:36]=3[Cl:48])[CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].[C:49](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:14]([NH:17][C:18]1[N:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([NH:28][CH2:29][C:30]2[N:31]([C:35]3[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([CH:42]([O:1][C:2]4[C:10]5[N:9]=[C:8]([O:11][CH3:12])[NH:7][C:6]=5[CH:5]=[CH:4][CH:3]=4)[CH3:49])[C:36]=3[Cl:48])[CH:32]=[CH:33][CH:34]=2)=[O:27])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 106548994-hydroxy-2-methoxy-1-methyl-1H-benzimidazoleHCID 183217612-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole

Produkt 1

HCID 183218612-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrroleAusbeute 23,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxy-2-methoxy-1-methyl-1H-benzimidazole (47.4 mg), 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(methanesulfonyloxymethyl)phenyl]pyrrole (143 mg) and potassium carbonate (110 mg) in N,N-dimethylformamide (4 ml) was stirred at ambient temperature for 3.5 days. The mixture was partitioned between chloroform and water. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V) to give 2-[(E)-3-(6-acetamidopyridin-3-yl)acryloylaminomethyl]-1-[2,4-dichloro-3-(2-methoxy-1-methyl-1H-benzimidazol-4-yloxymethyl)phenyl]pyrrole (39 mg) as colorless crystals.

Aufarbeitung

  1. customThe mixture was partitioned between chloroform and water
  2. dry with materialThe separated organic layer was dried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=9:1, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-c1c3f63c81ce4b5ca25eacca15aa3588
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06100284

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