Anisole → HCID 57387081, compound

HRID 1800622Notes

Reaction equation

HRID 1800622 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:25]([CH:27]4[CH2:29][CH2:28]4)=[O:26])=[N:23][C:18]3=[CH:17][CH:16]=2)[CH:9]=1)(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][C:15]1[N:20]=[C:19]2[S:21][C:22]([NH:24][C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])=[N:23][C:18]2=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 57388053HCID 57388053, compound

Product 1

HCID 57387081HCID 57387081, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)phenyl]carbamate (900 mg, 2.11 mmol) and anisole (1 mL) in trifluoroacetic acid (10 mL) was stirred at 0° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (50 mL) was added to the residue, and the mixture was extracted with tetrahydrofuran-ethyl acetate mixture (1:1, 50 mL, 15 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with a tetrahydrofuran-ethyl acetate mixture to give the title compound (542 mg, 79%) as a pale-yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate solution (50 mL)
  2. additionwas added to the residue
  3. extractionthe mixture was extracted with tetrahydrofuran-ethyl acetate mixture (1:1, 50 mL, 15 mL)
  4. washThe combined organic layer was washed with saturated brine (5 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with a tetrahydrofuran-ethyl acetate mixture

Sources & evidence

ORD record
ord-624e98c83bf04661b614d44f3c7dbf86
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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