Trifluoroacetic acid → HCID 59152195, compound

HRID 605588Notes

Reaction equation

HRID 605588 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14](/[N:16]=[C:17]2\[S:18][CH:19]=[CH:20][N:21]\2[CH2:22][O:23][CH3:24])[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl.CO>[CH3:24][O:23][CH2:22][N:21]1[CH:20]=[CH:19][S:18]/[C:17]/1=[N:16]\[C:14]1[N:15]=[C:10]([CH2:9][OH:8])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57562623HCID 57562623, compound

Product 1

HCID 59152195HCID 59152195, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 14.28 g of 6-(((tert-butyl(dimethyl)silyl)oxy)methyl)-N-((2Z)-3-(methoxymethyl)-1,3-thiazol-2(3H)-ylidene)pyridin-2-amine in 30 ml of chloroform and 30 ml of methanol was added 30 ml of trifluoroacetic acid under cooling with ice, followed by stirring the reaction mixture at room temperature overnight. The reaction mixture was evaporated in vacuo. The resulting residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate =1/1) to give the title compound as a pale yellow solid.

Workup

  1. temperatureunder cooling with ice
  2. customThe reaction mixture was evaporated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resulting ethyl acetate solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane to hexane/ethyl acetate =1/1)

Sources & evidence

ORD record
ord-087bc98125024f408c372888f51665f8
Source dataset
uspto-grants-2011_03
Patent number
US07915263B2

Reaction notes

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