HCID 91594324, compound → HCID 86646032, compound

HRID 1800577Notes

Reaction equation

HRID 1800577 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[N:21]=[C:20]3[S:22][C:23]([NH:25][C:26](=[O:28])[CH3:27])=[N:24][C:19]3=[CH:18][CH:17]=2)[CH:9]=1)(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH:9]=1)[O:15][C:16]1[N:21]=[C:20]2[S:22][C:23]([NH:25][C:26](=[O:28])[CH3:27])=[N:24][C:19]2=[CH:18][CH:17]=1

Participants

3

Reactant 1

HCID 91594324HCID 91594324, compound

Product 1

HCID 86646032HCID 86646032, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-fluorophenyl)carbamate (1.05 g, 2.5 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 (0.78 g, 98%) as a pale-yellow 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-7bc8a78823b24032b53b8312897fa514
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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