3,5-Dimethylaniline → N-(3,5-Dimethylphenyl)-2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxamide

HRID 1984701

Reaktionsgleichung

Reaktionsgleichung von HRID 1984701
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[F:25][C:26]1[CH:31]=[C:30]([CH2:32][S:33][C:34]2[C:39]([C:40]([OH:42])=O)=[CH:38][CH:37]=[CH:36][N:35]=2)[CH:29]=[CH:28][N:27]=1.[NH2:43][C:44]1[CH:49]=[C:48]([CH3:50])[CH:47]=[C:46]([CH3:51])[CH:45]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH3:51][C:46]1[CH:45]=[C:44]([NH:43][C:40]([C:39]2[C:34]([S:33][CH2:32][C:30]3[CH:29]=[CH:28][N:27]=[C:26]([F:25])[CH:31]=3)=[N:35][CH:36]=[CH:37][CH:38]=2)=[O:42])[CH:49]=[C:48]([CH3:50])[CH:47]=1

Komponenten

7

Edukt 4

HCID 79493,5-DimethylanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 230940282-(2-Fluoropyridin-4-ylmethylthio)pyridine-3-carboxylic acid

Produkt 1

HCID 10067543N-(3,5-Dimethylphenyl)-2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxamideAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.0 g, 7.9 mmol) was added to a solution of 2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference compound No. 2-1, 1.5 g, 5.7 mmol), 3,5-xylidine (0.90 g, 7.4 mmol) and N,N-diisopropylethylamine (2.0 mL, 11 mmol) in N,N-dimethylformamide (20 mL) at room temperature, and the mixture was stirred for 12 hours. Ethyl acetate (30 mL) was added to the reaction mixture, the whole was washed with brine (50 mL), and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 0.91 g of the title reference compound as a colorless solid. (Yield 44%)

Aufarbeitung

  1. washthe whole was washed with brine (50 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe organic layer was evaporated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography
  5. customto give 0.91 g of the title reference compound as a colorless solid

Quellen und Nachweise

ORD-Eintrag
ord-ea30108da48641dab223eac646c5af13
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544703B2

Verknüpfte Notizen

Wird geladen…