Trifluoroacetic acid → N-[5-(3,5-Dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazol-3-yl]-1-(4-fluorophenyl)-methanesulfonamide

HRID 1038409Notes

Reaction equation

HRID 1038409 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][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)(=[O:28])=[O:27])[C:7]([C:37]#[N:38])=[C:6]([CH3:39])[NH:5][C:4]=1[CH3:40])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:37]([C:7]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][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)(=[O:27])=[O:28])[C:3]([C:1]#[N:2])=[C:4]([CH3:40])[NH:5][C:6]=1[CH3:39])#[N:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67023851tert-Butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-{[(4-fluorobenzyl)sulfonyl]-amino}-1H-indazole-1-carboxylate

Product 1

HCID 44547841N-[5-(3,5-Dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-1H-indazol-3-yl]-1-(4-fluorophenyl)-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

28 mg (0.05 mmol) tert-butyl 5-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)-3-{[(4-fluoro-benzyl)sulfonyl]amino}-1H-indazole-1-carboxylate (Example 13A), dissolved in dichloromethane (1 ml), were treated with 0.042 ml (0.55 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 10 mg (41% 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-315e12700794492fac9d733f5ed219be
Source dataset
uspto-grants-2013_10
Patent number
US08551989B2

Reaction notes

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