Trifluoroacetic acid → HCID 22063622, compound

HRID 1828545Notes

Reaction equation

HRID 1828545 reaction equation
[F:1][C:2]1[C:3]([CH2:16][CH2:17][C:18]2[S:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=2)=[CH:4][C:5]([NH:8]C(=O)OC(C)(C)C)=[N:6][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[C:3]([CH2:16][CH2:17][C:18]2[S:19][CH:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[N:22]=2)=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22063605HCID 22063605, compound2×

Product 1

HCID 22063622HCID 22063622, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The tert-butyl N-{5-fluoro-4-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-pyridyl}-carbamate (393 mg, 1.08 mmol) obtained in (G) was dissolved in methylene chloride (10 ml), added with trifluoroacetic acid (10 ml) under ice cooling, and stirred overnight at room temperature. The reaction mixture was concentrated, and the resulting residue was dissolved in chloroform and washed with 1 N aqueous sodium hydroxide. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:2) to obtain the title compound (40.0 mg, 33%) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in chloroform
  3. washwashed with 1 N aqueous sodium hydroxide
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:2)

Sources & evidence

ORD record
ord-c075e2e68239482b9c45ad877d55b54f
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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