Ethyl Acetate → N-(2-fluorobenzyl)-2-[1-neopentyl-2-oxo-4-(pyridin-4-ylmethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl]acetamide

HRID 1863989

Reaktionsgleichung

Reaktionsgleichung von HRID 1863989
[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][NH:5][C:6](=[O:33])[CH2:7][CH:8]1[N:14]([C:15](=O)[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:13][C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:9]1=[O:32].Br.BrCC1C=CN=CC=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:1][C:2]1[CH:37]=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][NH:5][C:6](=[O:33])[CH2:7][CH:8]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:13][C:12]2[CH:23]=[CH:24][CH:25]=[CH:26][C:11]=2[N:10]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:9]1=[O:32]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 127522194-(Bromomethyl)pyridine hbrHCID 23089896N-(2-fluorobenzyl)-2-(4-isonicotinoyl-1-neopentyl-2-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl)acetamide

Produkt 1

HCID 67178144N-(2-fluorobenzyl)-2-[1-neopentyl-2-oxo-4-(pyridin-4-ylmethyl)-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-3-yl]acetamideAusbeute 42,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound (0.36 g) obtained in Example 1B (1) in dimethylformamide (15 ml) were added 4-(bromomethyl)pyridine hydrobromide (0.92 g) and potassium carbonate (0.87 g), and the mixture was stirred at room temperature for 20 hrs. Ethyl acetate was added, and the mixture was washed with water and dried over anhydrous MgSO4. The solvent was evaporated, and the residue was purified by silica gel column chromatography and recrystallized from hexane-chloroform to give the title compound (0.15 g) as colorless crystals.

Aufarbeitung

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography
  5. customrecrystallized from hexane-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-c38ab279bf744a689fc9fb125fe64f40
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07625887B2

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