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

Reaction equation

HRID 1863989 reaction equation
[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]

Participants

6

Reactant 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

Product 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]acetamideYield 42.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c38ab279bf744a689fc9fb125fe64f40
Source dataset
uspto-grants-2009_12
Patent number
US07625887B2

Linked notes

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