Triethylamine → (4-{2-[(4-bromophenyl)methyl]-1-methylbenzimidazol-5-yloxy)-(2-pyridyl))-N-methylcarboxamide

HRID 13489

Reaktionsgleichung

Reaktionsgleichung von HRID 13489
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=O)=[CH:4][CH:3]=1.[C:12](Cl)(=O)C(Cl)=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH:33]=[CH:34][C:35]=1[NH2:36])[O:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=1.C(N(CC)CC)C>ClCCl.O1CCCC1.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[N:36]([CH3:12])[C:35]3[CH:34]=[CH:33][C:21]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([C:29]([NH:31][CH3:32])=[O:30])[CH:24]=4)=[CH:20][C:19]=3[N:18]=2)=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 177564924-(3,4-Diamino-phenoxy)-pyridine-2-carboxylic acid methylamide

Produkt 1

HCID 22040593(4-{2-[(4-bromophenyl)methyl]-1-methylbenzimidazol-5-yloxy)-(2-pyridyl))-N-methylcarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To 4-bromophenyl acetic acid (1 eq) in dichoromethane containing a drop of N,N-dimethyl formamide at 0° C. was added oxalyl chloride (1.2 eq). The resulting mixture was then brought to ambient temperature and stirred for 2 h. The mixture was concentrated and to it was added tetrahydrofuran and [4-(3,4-diaminophenoxy)(2-pyridyl)]-N-methylcarboxamide (1 eq) and triethyl amine (1 eq) and stirred for 2 h. Formation of the N-acylated product was followed by LC/MS. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was dried with sodium sulfate and concentrated and taken in acetic acid and heated to 60° C. for 2 h. Preparative chromatography yielded (4-{2-[(4-bromophenyl)methyl]-1-methylbenzimidazol-5-yloxy)-(2-pyridyl))-N-methylcarboxamide. MS: MH+=451.

Aufarbeitung

  1. customwas then brought to ambient temperature
  2. concentrationThe mixture was concentrated and to it
  3. stirringstirred for 2 h
  4. concentrationThe mixture was concentrated
  5. custompartitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-22061ce98fb743848674799c608f787f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728010B2

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