Benzylamine → 2-(Benzylamino)-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

HRID 1635487Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1635487
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:21]([NH:28][C:2]1[CH:7]=[C:6]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=3)[N:11]=[C:10]([CH3:20])[CH:9]=2)[CH:5]=[CH:4][N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

3

Edukt 2

HCID 7504Benzylamine2×HCID 114829832-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Produkt 1

HCID 98415332-(Benzylamino)-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridineAusbeute 85 %

Versuchsvorschrift

A mixture of 2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine (Example 45; 1.24 g, 0.0044 mol) and benzylamine (40 mL) was heated at 180° C. for 20 hours The excess benzylamine was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude product was purified by chromatography on silica gel (ethyl acetate/hexane, 3:7) to give 1.33 g (85% yield) of the titled compound as a clear oil, which solidified upon standing: mp: 73-75° C. Anal. Calc'd. for C23H22N40.2H2O: C, 76.83; H, 6.39; N, 15.06. Found: C, 76.88; H, 6.37; N, 14.92.

Aufarbeitung

  1. customwas removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was purified by chromatography on silica gel (ethyl acetate/hexane, 3:7)

Quellen und Nachweise

ORD-Eintrag
ord-944c39dc0a564d278a72e8d3c7c516db
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06509361B1

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