Trifluoroacetic acid → HCID 24954184, compound

HRID 391555Notes

Reaction equation

HRID 391555 reaction equation
[CH3:1][S:2](=[N:10][C:11]([C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:21]2[S:25][C:24]([NH:26]C(=O)OC(C)(C)C)=[N:23][CH:22]=2)[CH:16]=[N:17][CH:18]=1)=[O:12])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:26][C:24]1[S:25][C:21]([C:20]#[C:19][C:15]2[CH:16]=[N:17][CH:18]=[C:13]([CH:14]=2)[C:11]([N:10]=[S@@:2]([CH3:1])(=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12])=[CH:22][N:23]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 74372495HCID 74372495, compound

Product 1

HCID 24954184HCID 24954184, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing tert-butyl (5-{[5-({[methyl(oxo)phenyl-λ6-sulfanylidene]amino}carbonyl)pyridin-3-yl]ethynyl}-1,3-thiazol-2-yl)carbamate (16 mg, 0.032 mmol) in 2.0 mL dichloromethane at room temperature was added trifluoroacetic acid (0.099 mL, 1.3 mmol). The reaction was stirred at room temperature for 17 hours, then partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, dried with anhydrous Na2SO4 and rotary evaporated. The resulting solid film was purified by chromatography (silica gel, CHCl3/EtOAc) to give the title compound as a tan solid (9 mg, 74%).

Workup

  1. custompartitioned between EtOAc and saturated NaHCO3 solution
  2. washThe EtOAc layer was washed with H2O, brine
  3. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  4. customThe resulting solid film was purified by chromatography (silica gel, CHCl3/EtOAc)

Sources & evidence

ORD record
ord-6e41989b44ea404bb65e61db69d585da
Source dataset
uspto-grants-2013_02
Patent number
US08383825B2

Reaction notes

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