Trifluoroacetic acid → HCID 178434354, compound

HRID 1691809Notes

Reaction equation

HRID 1691809 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([N:14]1[CH:19]=[CH:18][C:17](=[O:20])[CH2:16][C@H:15]1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:13])[N:7](S(C1C=CC(C)=CC=1)(=O)=O)[N:6]=[C:5]2[CH3:38].FC(F)(F)C(O)=O>CSC>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([N:14]1[CH:19]=[CH:18][C:17](=[O:20])[CH2:16][C@H:15]1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:13])[NH:7][N:6]=[C:5]2[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59377758(S)-2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid [5-bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-yl]-amide

Product 1

HCID 178434354HCID 178434354, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 1068Dimethyl SulfideSolvent

Procedure

(S)-2-(4-Fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid [5-bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-yl]-amide (40 mg, 0.07 mmol) was dissolved in dimethylsulfide (5 ml) at room temperature. Trifluoroacetic acid (1 ml) was added and the mixture was allowed to stir at room temperature overnight. The solution was concentrated in vacuo, and the residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate) to give (S)-2-(4-fluoro-phenyl)-4-oxo-3,4-dihydro-2H-pyridine-1-carboxylic acid (5-bromo-3-methyl-1H-indazol-6-yl)-amide 30 mg (90.0%) of an off-white foam. MS (ES+) m/z 443 (M+H).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue was purified by flash chromatography (gradient 9:1 to 1:1 Hexanes/Ethyl Acetate)

Sources & evidence

ORD record
ord-6543aaa8272d487fa75aceaf0490d515
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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