Trifluoroacetic acid → HCID 54765519, compound

HRID 509098Notes

Reaction equation

HRID 509098 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=2[S:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([S:26]([N:29](CC3C=CC(OC)=CC=3OC)[C:30]3[S:31][CH:32]=[N:33][N:34]=3)(=[O:28])=[O:27])=[C:21]([F:46])[CH:20]=2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[ClH:25].[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([F:15])([F:16])[F:17])[CH:11]=[CH:10][C:9]=2[S:18][C:19]2[C:24]([Cl:25])=[CH:23][C:22]([S:26]([NH:29][C:30]3[S:31][CH:32]=[N:33][N:34]=3)(=[O:28])=[O:27])=[C:21]([F:46])[CH:20]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68042650HCID 68042650, compound

Product 1

HCID 54765519HCID 54765519, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-{[2-(2-Aminopyridin-4-yl)-4-(trifluoromethyl)phenyl]thio}-5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 26, 0.153 g, 74.4 mmol) was dissolved in dichloromethane (3 mL). Trifluoroacetic acid (3 mL) was added and the mixture stirred at room temperature under nitrogen for 3 hours. Solvents were removed in vacuo and the residue diluted in ethyl acetate (10 mL) before washing with an aqueous solution of hydrochloric acid (10 mL, 2.0 M). The organic layer was collected, dried over sodium sulphate, filtered and concentrated in vacuo. The title compound was purified by trituration in a mixture of tert-butylmethylether and dichloromethane (2:1) to give the title compound as a white solid (0.021 g, 15%).

Workup

  1. customSolvents were removed in vacuo
  2. additionthe residue diluted in ethyl acetate (10 mL)
  3. washbefore washing with an aqueous solution of hydrochloric acid (10 mL, 2.0 M)
  4. customThe organic layer was collected
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe title compound was purified by trituration in a mixture of tert-butylmethylether and dichloromethane (2:1)

Sources & evidence

ORD record
ord-cffa65c6a3e241bc9554264a69acfe01
Source dataset
uspto-grants-2015_08
Patent number
US09096558B2

Reaction notes

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