HCID 91433615, compound → HCID 86646036, compound

HRID 1800589Notes

Reaction equation

HRID 1800589 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)[C:11]([F:28])=[CH:10][C:9]=1[F:29])(C)(C)C>FC(F)(F)C(O)=O>[NH2:7][C:8]1[C:9]([F:29])=[CH:10][C:11]([F:28])=[C:12]([CH:13]=1)[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 91433615HCID 91433615, compound

Product 1

HCID 86646036HCID 86646036, 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]-2,4-difluorophenyl}carbamate (4.36 g, 10.0 mmol) in trifluoroacetic acid (20 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 (200 mL), washed with 0.1N aqueous sodium hydroxide solution (200 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 (3.37 g, quantitatively) as a white amorphous.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (200 mL)
  3. washwashed with 0.1N aqueous sodium hydroxide solution (200 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-64e0927d78094d79b2a9d9a4a8050c5b
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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