Pyridine → HCID 23499177, compound

HRID 1597374Notes

Reaction equation

HRID 1597374 reaction equation
[CH3:1][N:2]([CH3:30])[S:3]([N:6]1[CH:10]=[C:9]([CH:11]([OH:22])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[N:8]=[C:7]1[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])(=[O:5])=[O:4].N1C=CC=CC=1.[C:37](Cl)(=[O:39])[CH3:38]>C1(C)C=CC=CC=1>[Si:23]([C:7]1[N:6]([S:3](=[O:4])(=[O:5])[N:2]([CH3:30])[CH3:1])[CH:10]=[C:9]([CH:11]([O:22][C:37](=[O:39])[CH3:38])[C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[N:8]=1)([C:26]([CH3:27])([CH3:29])[CH3:28])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 54026974HCID 54026974, compound

Product 1

HCID 23499177HCID 23499177, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2-(tert-Butyldimethylsilyl)-4-(hydroxyquinolin-4-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (example 8, step A) (0.750 g, 1.62 mmol) in 8 ml of anhydrous toluene at 0° C., pyridine (0.16 ml, 1.94 mmol) was added followed by acetyl chloride (0.14 ml, 1.94 mmol). The solution was stirred at room temperature for two hours. It was cooled to 0° C. and ice cubes were added. The reaction mixture was partitioned between toluene (5 ml) and water (5 ml). The organic layer was dried over sodium sulfate, filtered, concentrated under reduced pressure and column purified (hexanes:EtOAc; 1:4) to give 0.84 g (100%) of the product.

Workup

  1. temperatureIt was cooled to 0° C.
  2. additionice cubes were added
  3. customThe reaction mixture was partitioned between toluene (5 ml) and water (5 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure and column
  7. custompurified (hexanes:EtOAc; 1:4)

Sources & evidence

ORD record
ord-0ed4206c82554650a9cd66ab192f954a
Source dataset
uspto-grants-2001_09
Patent number
US06294566B1

Reaction notes

Loading…