Methyl iodide → HCID 67215732, compound

HRID 1677566Notes

Reaction equation

HRID 1677566 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=3)[C:25]([O:27][CH3:28])=[O:26])=[O:19])=[N:16][CH:17]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:35]I.S([O-])(O)(=O)=O.[K+]>CN(C)C=O>[C:1]([O:5][C:6]([N:8]([CH3:35])[C:9]1[CH:10]=[CH:11][C:12]2[N:13]([C:15]([C:18]([C:20]3[CH:21]=[CH:22][C:23]([N+:30]([O-:32])=[O:31])=[C:24]([CH:29]=3)[C:25]([O:27][CH3:28])=[O:26])=[O:19])=[N:16][CH:17]=2)[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 67215620HCID 67215620, compound

Product 1

HCID 67215732HCID 67215732, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

540 mg (1.23 mmol) of methyl 5-({6-[(tertbutoxycarbonyl)amino]imidazo[1,5-a]pyridin-3-yl}carbonyl)-2-nitrobenzoate in 10 ml of dimethylformamide are added to 53.9 mg (1.35 mmol) of sodium hydride (60% dispersion in oil) in 2 ml of dimethylformamide, the mixture is stirred at ambient temperature for 30 minutes, then 84 μl (1.35 mmol) of methyl iodide are added and the mixture is left stirring at ambient temperature overnight. The mixture is acidified to pH=4 with an aqueous potassium hydrogensulfate solution and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under reduced pressure. The product is purified by filtration through a bed of silica, elution being carried out with dichloromethane. 475 mg of an orange-colored powder are obtained. Melting point: 55° C.; 1H NMR (d6-DMSO): 1.46 (9H, s), 3.33 (3H, s), 3.92 (3H, s), 7.57 (1H, d), 7.98 (1H, s), 8.06 (1H, d), 8.25 (1H, d), 8.68 (1H, d), 8.76 (1H, s), 9.77 (1H, s)

Workup

  1. waitthe mixture is left
  2. stirringstirring at ambient temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe product is purified by filtration through a bed of silica, elution

Sources & evidence

ORD record
ord-ddefd11d531b4f2db5f94807767a9b48
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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