Trifluoroacetic acid → N-[5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazol-3-yl]propane-1-sulfonamide

HRID 1038413Notes

Reaction equation

HRID 1038413 reaction equation
[C:1]([C:3]1[CH:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14](C(OC(C)(C)C)=O)[N:13]=[C:12]3[NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[C:7]([C:32]#[N:33])=[C:6]([CH3:34])[NH:5][C:4]=1[CH3:35])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([C:3]1[CH:8]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][N:13]=[C:12]3[NH:25][S:26]([CH2:29][CH2:30][CH3:31])(=[O:28])=[O:27])[C:7]([C:32]#[N:33])=[C:6]([CH3:34])[NH:5][C:4]=1[CH3:35])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67023831tert-Butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-[(propylsulfonyl)amino]-1H-indazole-1-carboxylate

Product 1

HCID 44547689N-[5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazol-3-yl]propane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

57.8 mg (0.12 mmol) tert-butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-[(propyl-sulfonyl)amino]-1H-indazole-1-carboxylate (Example 20A) were dissolved in dichloromethane (4 ml) and treated with 0.1 ml (1.28 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 purified by preparative RP-HPLC (acetonitrile/water gradient) to give 13 mg (29% 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. customThe residue was purified by preparative RP-HPLC (acetonitrile/water gradient)

Sources & evidence

ORD record
ord-683d945a65624333af5a550481225859
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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