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3-Chloro-2-methylaniline → Friluglanstat

HRID 1505771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505771
[CH3:1][O:2][CH2:3][C:4]1[NH:8][C:7]2[CH:9]=[C:10]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:28])([F:27])[F:26])=[O:18])[CH:11]=[C:12]([C:13]([OH:15])=O)[C:6]=2[N:5]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:53][C:54]1[C:55]([CH3:61])=[C:56]([CH:58]=[CH:59][CH:60]=1)[NH2:57].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[Cl:53][C:54]1[C:55]([CH3:61])=[C:56]([NH:57][C:13]([C:12]2[C:6]3[N:5]=[C:4]([CH2:3][O:2][CH3:1])[NH:8][C:7]=3[CH:9]=[C:10]([NH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]([F:26])([F:28])[F:27])=[O:18])[CH:11]=2)=[O:15])[CH:58]=[CH:59][CH:60]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 68943-Chloro-2-methylanilineHCID 516892Sodium BicarbonateHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90229242HCID 90229242, Verbindung

Produkt 1

HCID 71267445Friluglanstat

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of 2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxylic acid (153 mg) in DMF (5 mL), were added HBTU (178 mg) and triethylamine (65 μL). To the mixture was added 3-chloro-2-methylaniline (56 μL) under stirring at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified on silica gel column chromatography to obtain N-(3-chloro-2-methylphenyl)-2-(methoxymethyl)-6-({[2-(trifluoromethyl)phenyl]carbonyl}amino)-1H-benzimidazole-4-carboxamide (165 mg) as colorless powder.

Aufarbeitung

  1. stirringthe mixture was stirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified on silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b3467955550c47bf8d25d926ba6d05cd
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216968B2

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