HCID 91325177, compound → N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]propanamide

HRID 1800615Notes

Reaction equation

HRID 1800615 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:29])=[CH:10][C:9]=1[F:30])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:30])=[CH:10][C:11]([Cl:29])=[C:12]([CH:13]=1)[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25](=[O:28])[CH2:26][CH3:27])=[N:23][C:18]2=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 91325177HCID 91325177, compound

Product 1

HCID 86646047N-[5-(5-amino-2-chloro-4-fluorophenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]propanamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl(4-chloro-2-fluoro-5-{[2-(propanoylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}phenyl)carbamate (1.26 g, 2.70 mmol) and trifluoroacetic acid (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with aqueous sodium hydrogen carbonate solution (30 mL×2) and saturated brine (10 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=67/33→0/100) to give the title compound (787 mg, 79%) as white crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  3. washThe solution was washed with aqueous sodium hydrogen carbonate solution (30 mL×2) and saturated brine (10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=67/33→0/100)

Sources & evidence

ORD record
ord-6f74564a737a49a698fffd62ba6d788c
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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