4-Bromoaniline → N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 1410245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1410245
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[NH:17][C:18]1[N:22]([CH3:23])[C:21]2[CH:24]=[C:25]([O:31][CH2:32][CH:33]([F:35])[F:34])[C:26]([C:28](O)=[O:29])=[CH:27][C:20]=2[N:19]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:60][C:61]1[CH:67]=[CH:66][C:64]([NH2:65])=[CH:63][CH:62]=1>CN(C=O)C.[Cl-].[Na+].O>[Br:60][C:61]1[CH:67]=[CH:66][C:64]([NH:65][C:28]([C:26]2[C:25]([O:31][CH2:32][CH:33]([F:34])[F:35])=[CH:24][C:21]3[N:22]([CH3:23])[C:18]([NH:17][C:3]4[CH:4]=[C:5]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH:6]=[CH:7][C:2]=4[Cl:1])=[N:19][C:20]=3[CH:27]=2)=[O:29])=[CH:63][CH:62]=1

Komponenten

6

Edukt 3

HCID 78074-BromoanilineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866463402-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid

Produkt 1

HCID 86646339N-(4-Bromo-phenyl)-2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-chloro-5-{[(tert-butoxycarbonyl)-amino]-methyl}-phenylamino)-6-(2,2-difluoro-ethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid (1.12 g; 2.19 mmol), HBTU (831 mg; 2.19 mmol) and TEA (433 mg; 4.38 mmol) in DMF (10 mL) was stirred for 30 min at rt and thereafter added to a solution of 4-bromoaniline (377 mg; 2.19 mmol) in DMF (10 mL). The resulting mixture was stirred over night at rt, poured into brine and extracted with EtOAc. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give the sub-title compound. Yield: 1.35 g (93%).

Aufarbeitung

  1. stirringThe resulting mixture was stirred over night at rt
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-30c7fdd20980419ba1ceb34e236d8cad
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921405B2

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