Dimethylformamide → HCID 67279747, compound

HRID 1693286Notes

Reaction equation

HRID 1693286 reaction equation
[H-].[Na+].[OH:3][CH:4]1[C:13]2[CH2:12][S:11][N:10]=[C:9]([N:14](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)[C:8]3=[N:29][N:30]([CH2:32][C:33]4[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([CH3:42])=[CH:35][N:34]=4)[N:31]=[C:6]([C:7]=23)[CH2:5]1.[CH3:43]N(C)C=O.CI>O>[CH3:43][O:3][CH:4]1[C:13]2[CH2:12][S:11][N:10]=[C:9]([NH2:14])[C:8]3=[N:29][N:30]([CH2:32][C:33]4[C:38]([CH3:39])=[C:37]([O:40][CH3:41])[C:36]([CH3:42])=[CH:35][N:34]=4)[N:31]=[C:6]([C:7]=23)[CH2:5]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86641323HCID 86641323, compound

Product 1

HCID 67279747HCID 67279747, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (6.7 mg) was added to a mixture of di-tert-butyl {8-hydroxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7,8,9-tetrahydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-4-yl}imidodicarbonate of Example 32 (40 mg) and dehydrated N,N-dimethylformamide (1 mL), and then the mixture was stirred at room temperature for one hour. Methyl iodide (6.5 μL) was added to the reaction mixture, followed by stirring for 1.5 hours. Then, water (20 mL) was added. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. Dichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) were added to the resulting residue, and the mixture was stirred at room temperature for two hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by reversed phase liquid chromatography to obtain the title compound (4.8 mg, 18%) as a solid.

Workup

  1. stirringby stirring for 1.5 hours
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. additionDichloromethane (2 mL) and trifluoroacetic acid (0.5 mL) were added to the resulting residue
  8. stirringthe mixture was stirred at room temperature for two hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe resulting residue was purified by reversed phase liquid chromatography

Sources & evidence

ORD record
ord-1f7fa4ff1dcc434587a964a061f14e9d
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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