Water → HCID 59570918, compound

HRID 2192901Notes

Reaction equation

HRID 2192901 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([OH:11])[N:5]=2.C(=O)([O-])[O-].[K+].[K+].[C:18]([O:21][CH2:22][CH2:23]Br)(=[O:20])[CH3:19].O>CN(C=O)C.[Cl-].[Na+].O>[C:18]([O:21][CH2:22][CH2:23][O:11][C:6]1[N:5]=[C:4]2[S:3][C:2]([NH2:1])=[N:10][C:9]2=[CH:8][CH:7]=1)(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178508197HCID 178508197, compound

Product 1

HCID 59570918HCID 59570918, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino[1,3]thiazolo[5,4-b]pyridin-5-ol 2 hydrobromide (10 g) in DMF (20 mL) were added potassium carbonate (25.2 g) and 2-bromoethyl acetate (4 mL) at room temperature. It was stirred at 80° C. for 2 hours. To the reaction mixture were added saturated brine and water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=1:2-1:3) to obtain 2-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]ethyl acetate (2.97 g) as a pale yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:2-1:3)

Sources & evidence

ORD record
ord-9867b0e47e384c529ff8c5e7b8f823de
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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