Chlorosuccinimide → 6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-(5-chlorothiazol-2-yl)pyridin-2-amine

HRID 1725479Notes

Reaction equation

HRID 1725479 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:22]N1C(=O)CCC1=O>O1CCOCC1.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([NH:16][C:17]2[S:18][C:19]([Cl:22])=[CH:20][N:21]=2)[CH:13]=[CH:12][CH:11]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 57562580HCID 57562580, compound

Product 1

HCID 575626076-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-(5-chlorothiazol-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

2 g of 6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-thiazol-2-ylpyridin-2-amine obtained in Example 5-(2) was dissolved in 20 ml of 1,4-dioxane, and then 832 mg of N-chlorosuccinimide was added thereto at room temperature. The reaction mixture was heated under reflux for 2 hours, cooled to room temperature, diluted with ethyl acetate, and then washed with water and brine. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated in vacuo to give the title compound.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. washwashed with water and brine
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b86519f04cc64dc4874860a435bde1f9
Source dataset
uspto-grants-2009_02
Patent number
US07491720B2

Reaction notes

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