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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-amino-2-hydroxybenzamide

HRID 1505208
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1505208
[NH2:1][C:2]1[C:3]([OH:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.CCN=C=NCCCN(C)C.OC1C2N=NNC=2C=CC=1.[F:33][C:34]([F:50])([F:49])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[C:37]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH:36]=1>CN(C=O)C>[F:49][C:34]([F:33])([F:50])[C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH:42][C:5](=[O:7])[C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[C:3]=2[OH:11])=[C:37]([N:43]2[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]2)[CH:36]=1
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Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 684433-Aminosalicylic acidHCID 58873623(4-(Trifluoromethyl)-2-(piperidin-1-yl)phenyl)-methanamineHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 67424346N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-amino-2-hydroxybenzamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-amino-2-hydroxybenzoic acid (1 g, 6.5 mmol) was dissolved in 20 ml of DMF and at 0° C. EDCI (1.4 g, 1.2 equiv.), hydroxybenzotriazole (1 g, 1.2 equiv.) and amine 2c (2 g, 1.2 equiv.) were added. The mixture was stirred at rt for 20 hours. The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt 1/petroleum ether 9 as eluant gave 1.3 g of a beige solid. Yield=51% [M+1] 393.4 (C20H22F3N3O2 requires 393.4).

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe crude was dissolved in AcOEt (30 ml)
  3. washwashed with water (1×20 ml) and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe purification of the crude residue by chromatographic column

Quellen und Nachweise

ORD-Eintrag
ord-170d385d9a9b4db4bd62dc876647e187
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09216975B2

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