Dimethylformamide → Srpin614

HRID 2099092Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2099092
[H-].[Na+].[CH3:3]N(C)C=O.[N:8]1([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[NH:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.CI>O>[CH3:3][N:24]([C:15]1[CH:16]=[C:17]([C:20]([F:23])([F:21])[F:22])[CH:18]=[CH:19][C:14]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:25](=[O:32])[C:26]1[CH:27]=[CH:28][N:29]=[CH:30][CH:31]=1

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2797577Srpin340

Produkt 1

HCID 23149643Srpin614Ausbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (60% (w/w) oil mixture) (200 mg, 0.500 mmol) was added at 0° C. to an N,N-dimethylformamide (DMF; 0.5 ml) solution of 5 N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]isonicotinamide (SRPIN-1, GIF-0340) (121 mg, 0.496 mmol), obtained as described in Referential example 1-3. The resulting mixture was stirred for one hour, and an N,N-dimethylformamide (DMF) solution of methyl iodide (0.8 M, 0.62 ml, 0.496 mmol) was added thereto at 0° C. The resulting mixture was stirred for three hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (12 g, hexane/ethyl acetate=1/1). Thus, N-methyl-N-[2-(1-piperidinyl)-5-(trifluoromethyl)phenyl]isonicotinamide (GIF-0614) (65.9 mg, 51.5%) was yielded as a colorless solid.

Aufarbeitung

  1. customobtained
  2. customat 0° C
  3. stirringThe resulting mixture was stirred for three hours
  4. extractionthe resulting mixture was extracted three times with ethyl acetate
  5. washThe obtained organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (12 g, hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-1d2ba75155b34da0b21daac004c32eff
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569536B2

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