Methyl iodide → benzyl 8-bromo-1,5-dimethyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-ylcarbamate

HRID 899401Notes

Reaction equation

HRID 899401 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([CH3:23])=[N:7][CH:8]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[C:26](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[C:6]([CH3:23])=[N:7][CH:8]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9](=[O:11])[N:10]([CH3:26])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135850842HCID 135850842, compound

Product 1

HCID 21941566benzyl 8-bromo-1,5-dimethyl-2-oxo-2,3-dihydro-1H-1,4-benzodiazepin-3-ylcarbamateYield 77.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product of Step 2 (2.0 g, 4.98 mmol) was dissolved in anhydrous N,N-dimethylformamide (10 ml). To this solution was added potassium carbonate (1.72 g, 12.44 mmol) and iodomethane (0.847 g, 5.97 mmol), and the reaction mixture was sealed in a pressure flask and stirred for 12 hours at room temperature, then diluted with water and ethyl acetate (20/70 ml). The aqueous solution was then extracted with ethyl acetate (3×20 ml). The organic layers were combined, washed with water (1×100 ml), dried over magnesium sulfate, filtered and concentrated to give the title compound (1.58 g, 77.5%). 1H NMR (CDCl3, 300 MHz): δ 7.43-7.28 (m, 7 H), 6.68 (d, 1H, J=8.1 Hz), 5.15-5.05 (m, 3H), 3.38 (s, 3H), 2.45 (d, 3H, 1.5 Hz) ppm.

Workup

  1. customthe reaction mixture was sealed in a pressure flask
  2. extractionThe aqueous solution was then extracted with ethyl acetate (3×20 ml)
  3. washwashed with water (1×100 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43f3a0eeb6c54c8dab4111f01590f833
Source dataset
uspto-grants-2008_04
Patent number
US07354914B2

Reaction notes

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