Sodium hydride → HCID 9842942, compound

HRID 1814065Notes

Reaction equation

HRID 1814065 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[CH:13]=[C:12]([C:14]3[N:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][C:8]2=[N:9][CH:10]=1)(=[O:4])=[O:3].[H-].[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][N:11]2[C:8]3=[N:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[C:7]3[CH:13]=[C:12]2[C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 516892Sodium BicarbonateHCID 15486862HCID 15486862, compound

Product 1

HCID 9842942HCID 9842942, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound obtained in Example 6 (3) (3.0 mg) in N,N-dimethylformamide (0.5 ml), 60% sodium hydride (0.7 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred at the same temperature for 15 minutes. 4-Fluorobenzyl bromide (3.1 mg) was then added thereto at 0° C. and the mixture was stirred at 15 to 30° C. for 1 hour. After completion of the reaction, the reaction solution was poured into a saturated aqueous sodium hydrogencarbonate solution and extracted with toluene. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (methanol:chloroform=1:20) to obtain 2.4 mg of the desired product as a white crystal.

Workup

  1. stirringat 0° C. and the mixture was stirred at 15 to 30° C. for 1 hour
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe organic layer was washed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was separated

Sources & evidence

ORD record
ord-549c0eb8d3e84443b2c1470993fcac2c
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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