Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate → HCID 86646025, compound

HRID 1800552Notes

Reaction equation

HRID 1800552 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:27])[CH3:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:11]=[CH:10][C:9]=1[F:28])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:13]=[C:12]([CH:11]=[CH:10][C:9]=1[F:28])[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25](=[O:27])[CH3:26])=[N:23][C:18]2=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 91133308Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate

Product 1

HCID 86646025HCID 86646025, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-2-fluorophenyl)carbamate (0.65 g, 1.54 mmol) in trifluoroacetic acid (5 mL) was stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (100 mL), washed with 0.1N aqueous sodium hydroxide solution (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (0.49 g, quantitatively) as a white amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with 0.1N aqueous sodium hydroxide solution (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-25ae3c24cb434d7681fe32403ecb814e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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