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Triethylamine → 3-[4-(2-Fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)urea

HRID 492671
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 492671
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH2:11])[CH:6]=1.[CH2:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])C.ClC([O:29][C:30]1C=CC=CC=1)=O.[CH3:36][NH:37][CH:38]1CCN(C)CC1>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:11][C:30](=[O:29])[N:37]([CH3:38])[CH:36]2[CH2:25][CH2:24][N:21]([CH3:19])[CH2:22][CH2:23]2)[CH:6]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 5663231-Methyl-4-(methylamino)piperidineHCID 231531982-Amino-4-(2-fluoro-4-nitrophenoxy)pyridine

Produkt 1

HCID 231533483-[4-(2-Fluoro-4-nitrophenoxy)pyridin-2-yl]-1-methyl-1-(1-methylpiperidin-4-yl)ureaAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(2-Fluoro-4-nitrophenoxy)pyridin-2-ylamine (200 mg) was dissolved in tetrahydrofuran (8 ml) under a nitrogen atmosphere, and then triethylamine (0.336 ml) and phenyl chloroformate (0.302 ml) were added dropwise thereto at room temperature, followed by stirring for 30 min. The reaction mixture was concentrated under a reduced pressure to give a residue, which was dissolved in N,N-dimethylformamide (5 ml), and then N-methyl-N-(1-methylpiperidin-4-yl)amine (0.467 ml) was added thereto at room temperature, followed by stirring for 4 hrs. The reaction mixture was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate). The resultant fractions were concentrated under a reduced pressure, and dried in vacuum to provide the titled compound (245 mg, 75.5%) as a yellow solid.

Aufarbeitung

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under a reduced pressure
  3. customto give a residue, which
  4. customat room temperature
  5. stirringby stirring for 4 hrs
  6. customThe reaction mixture was partitioned between ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride, water and brine in this order
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under a reduced pressure
  10. customto give a residue, which
  11. customwas purified by silica gel column chromatography (Fuji Silysia NH, eluent; ethyl acetate)
  12. concentrationThe resultant fractions were concentrated under a reduced pressure
  13. customdried in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2fd5762db30a49159984f08cbfb04a69
Quelldatensatz
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07531532B2

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