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Formaldehyde → 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(dimethylaminomethyl)-4-methylpyridine-2-carboxamide

HRID 1641748
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641748
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH2:18])=[O:17])=[N:14][CH:15]=1.[CH2:30]=O.Cl.[CH3:33][NH:34][CH3:35].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([S:20]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)(=[O:22])=[O:21])[C:10]1[C:11]([CH3:19])=[CH:12][C:13]([C:16]([NH:18][CH2:33][N:34]([CH3:30])[CH3:35])=[O:17])=[N:14][CH:15]=1
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Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 577364915-[(2,5-Difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide

Produkt 1

HCID 577364565-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-N-(dimethylaminomethyl)-4-methylpyridine-2-carboxamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxamide (150 mg, 0.33 mmol) obtained in Example 15 in N,N-dimethylformamide (3 ml), a formaldehyde solution (37%, 54 μl) and dimethylamine hydrochloride (136 mg, 1.67 mmol) were added at 0° C., and the mixture was stirred for 2 hours at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, and was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure, and the resulting residue was subjected to silica gel chromatography. The fraction obtained from an elution with dichloromethane:methanol=10:1 was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether and dichloromethane and dried, to obtain the title compound (99 mg, 0.21 mmol, 63%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. concentrationThe solvent was concentrated under reduced pressure
  4. customThe fraction obtained from an elution with dichloromethane
  5. concentrationmethanol=10:1 was concentrated under reduced pressure
  6. washthe resulting residue was washed with diethyl ether and dichloromethane
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a55462c74674461b9dccc5f1b92f632c
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114886B2

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