Water → 5-(3-cyanophenyl)-1-methyl-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione

HRID 1622315Notes

Reaction equation

HRID 1622315 reaction equation
O.[C:2]([C:4]1[CH:5]=[C:6]([N:10]2[C:16](=[O:17])[CH2:15][C:14](=[O:18])[NH:13][C:12]3[C:19]4[C:24]([CH:25]=[CH:26][C:11]2=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:7]=[CH:8][CH:9]=1)#[N:3].[H-].[Na+].I[CH3:30]>CS(C)=O.CCCCCC>[C:2]([C:4]1[CH:5]=[C:6]([N:10]2[C:16](=[O:17])[CH2:15][C:14](=[O:18])[N:13]([CH3:30])[C:12]3[C:19]4[C:24]([CH:25]=[CH:26][C:11]2=3)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:7]=[CH:8][CH:9]=1)#[N:3]

Participants

7

Reactant 4

HCID 962Water2×HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 468632195-(3-Cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione

Product 1

HCID 468633365-(3-cyanophenyl)-1-methyl-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dioneYield 27.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8058HexaneSolvent

Procedure

To a water-cooled solution of 5-(3-cyanophenyl)-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione (98 mg, 0.30 mmol) in DMSO (1 mL) was added 50-72% sodium hydride (12 mg). The mixture was stirred at room temperature for 1 hour, to which was added iodomethane (0.06 mL, 1 mmol). The mixture was stirred for 4 hours at room temperature, to which was added 50-72% sodium hydride (6 mg) and iodomethane (0.03 mL, 0.5 mmol). The mixture was stirred at room temperature for 18 hour, treated with cold water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was washed with ethyl acetate, then with hexane, to give 5-(3-cyanophenyl)-1-methyl-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione as a pale yellow crystal (28 mg, yield 27%). Then the solvent of washings was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1), to give 5-(3-cyanophenyl)-1,3-dimethyl-1H-naphtho[1,2-b][1,4]diazepin-2,4(3H,5H)-dione as a pale yellow oil (9 mg, yield 8%).

Workup

  1. stirringThe mixture was stirred for 4 hours at room temperature, to which
  2. stirringThe mixture was stirred at room temperature for 18 hour
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-9cd9a1d3202c4ddca55a4245bd71ee59
Source dataset
uspto-grants-2014_07
Patent number
US08778933B2

Reaction notes

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