Trifluoroacetic acid → HCID 67401257, compound

HRID 1186304Notes

Reaction equation

HRID 1186304 reaction equation
[F:1][C:2]([F:42])([F:41])[CH:3]([C:35]1[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=1)[O:4][C:5]1[C:6]([NH:15][S:16]([C:19]2[CH:34]=[CH:33][C:22]([CH2:23][CH2:24][NH:25]C(=O)OC(C)(C)C)=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.FC(F)(F)C(O)=O>ClCCl>[NH2:25][CH2:24][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([S:16]([NH:15][C:6]2[C:5]([O:4][CH:3]([C:35]3[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=3)[C:2]([F:41])([F:1])[F:42])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]=2)(=[O:17])=[O:18])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67401753HCID 67401753, compound2×

Product 1

HCID 67401257HCID 67401257, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(N-{3-[2,2,2-trifluoro-1-(pyridin-3-yl)ethoxy]quinoxalin-2-yl}sulfamoyl)phenethylcarbamate (Compound 208) was dissolved in dichloromethane (2 mL). To this, trifluoroacetic acid (2 mL) was added at room temperature and the mixture was stirred at room temperature for 24 hours. The solvent in the reaction mixture was evaporated off under reduced pressure, and purification by silica gel column chromatography (ethyl acetate/methanol=1/0 to 5/1) was performed to give 4-(2-aminoethyl)-N-{3-[2,2,2-trifluoro-1-(pyridin-3-yl)-ethoxy]quinoxalin-2-yl}benzenesulfonamide (Compound 209) (48 mg, 90%).

Workup

  1. customThe solvent in the reaction mixture was evaporated off under reduced pressure, and purification by silica gel column chromatography (ethyl acetate/methanol=1/0 to 5/1)

Sources & evidence

ORD record
ord-85d6c32c6a474f7ab02f9ef56cdce190
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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