Trifluoroacetic acid → HCID 67354964, compound

HRID 1038411Notes

Reaction equation

HRID 1038411 reaction equation
[CH3:1][CH:2]([CH3:43])[CH2:3][S:4]([N:7](S(CC(C)C)(=O)=O)[C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]3[C:22]([C:23]#[N:24])=[C:21]([CH3:25])[NH:20][C:19]([CH3:26])=[C:18]3[C:27]#[N:28])[CH:15]=2)[N:10](C(OC(C)(C)C)=O)[N:9]=1)(=[O:6])=[O:5].FC(F)(F)C(O)=O>ClCCl>[C:23]([C:22]1[CH:17]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[NH:7][S:4]([CH2:3][CH:2]([CH3:43])[CH3:1])(=[O:6])=[O:5])[C:18]([C:27]#[N:28])=[C:19]([CH3:26])[NH:20][C:21]=1[CH3:25])#[N:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67354846HCID 67354846, compound

Product 1

HCID 67354964HCID 67354964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

120 mg (0.19 mmol) tert-butyl 3-{bis[(2-methylpropyl)sulfonyl]amino}-5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazole-1-carboxylate (Example 18A) were dissolved in dichloromethane (4 ml) and treated with 0.161 ml (2.1 mmol) trifluoroacetic acid. The mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (4 ml), treated with 1 M aqueous lithium hydroxide solution (0.75 ml) and stirred at room temperature for 4 h. The mixture was then concentrated under reduced pressure, and the residue was purified by preparative RP-HPLC (acetonitrile/water gradient) to give 13 mg (16% of th.) of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in 1,4-dioxane (4 ml)
  9. additiontreated with 1 M aqueous lithium hydroxide solution (0.75 ml)
  10. stirringstirred at room temperature for 4 h
  11. concentrationThe mixture was then concentrated under reduced pressure
  12. customthe residue was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-292a1eeac337461f86fd500a1d663219
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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