3-Fluorobenzylamine → 2-(Dimethylaminomethyl)-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide

HRID 2093726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093726
C([O:3][C:4]([C:6]1[C:7]([CH2:21][N:22]([CH3:24])[CH3:23])=[N:8][C:9]2[C:14]([C:15]=1[CH3:16])=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)=O)C.C[Al](C)C.[F:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH2:33][NH2:34].CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.CCOC(C)=O.CO>[CH3:24][N:22]([CH2:21][C:7]1[C:6]([C:4]([NH:34][CH2:33][C:32]2[CH:35]=[CH:36][CH:37]=[C:30]([F:29])[CH:31]=2)=[O:3])=[C:15]([CH3:16])[C:14]2[C:9](=[CH:10][C:11]([C:17]([F:19])([F:20])[F:18])=[CH:12][CH:13]=2)[N:8]=1)[CH3:23]

Komponenten

7

Edukt 4

HCID 668533-FluorobenzylamineHCID 16682925TrimethylaluminumHCID 21226206Ethyl acetate hexaneHCID 665840092-((Dimethylamino)methyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

Produkt 1

HCID 568480832-(Dimethylaminomethyl)-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amideAusbeute 9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a stirred solution of 530 mg (1.56 mmol) 2-((dimethylamino)methyl)-4-methyl-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester in toluene (33 ml) were added 5.5 ml (2M solution in toluene, 10.9 mmol) Me3Al at RT followed by the addition of 1.77 g (15.6 mmol) 3-fluorobenzylamine. The reaction mixture was heated at 120° C. for 2 d. Then the reaction was quenched with water and acidified to pH ˜2 with conc. aq. HCl. After washing with EtoAc the aqueous layer was basified with NaOH to pH ˜11. The solution was then extracted twice with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4 and concentrated in vacuum. After CC (EtOAc/hexane 1:1->EtOAc/MeOH 9:1) of the residue, 60 mg (0.14 mmol, 9%) 2-(Dimethylaminomethyl)-N-[(3-fluorophenyl)-methyl]-4-methyl-7-(trifluoromethyl)-quinoline-3-carboxylic acid amide (example 31) were obtained. MS: m/z 420.2 [M+H]+.

Aufarbeitung

  1. customThen the reaction was quenched with water
  2. washAfter washing with EtoAc the aqueous layer
  3. extractionThe solution was then extracted twice with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-46a6096877f34a62933e068c9723068e
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445512B2

Notizen zur Reaktion

Wird geladen…