Trifluoroacetic acid → N-cyclopropyl-2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide

HRID 1051009Notes

Reaction equation

HRID 1051009 reaction equation
[CH:1]1([NH:4][C:5](=[O:39])[CH2:6][O:7][C:8]2[CH:9]=[C:10]([S:14]([N:17]3[C:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[F:28])=[CH:20][C:19]([CH2:29][N:30](C)[C:31](=O)OC(C)(C)C)=[CH:18]3)(=[O:16])=[O:15])[CH:11]=[CH:12][CH:13]=2)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([NH:4][C:5](=[O:39])[CH2:6][O:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([S:14]([N:17]3[CH:18]=[C:19]([CH2:29][NH:30][CH3:31])[CH:20]=[C:21]3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[F:28])(=[O:16])=[O:15])[CH:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90168590tert-butyl ((1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 74762997N-cyclopropyl-2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 3a (122 mg, 0.22 mmol) was dissolved in 8 mL of dichloromethane. The reaction solution was cooled in an ice bath, and 2 mL of trifluoroacetic acid were dropwise added. After removing the ice bath, the reaction solution was stirred at room temperature for 2 h. 20 mL of saturated sodium bicarbonate solution were added, and the reaction solution was extracted with dichloromethane (20 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system A to obtain the title product N-cyclopropyl-2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide 3 (80 mg, a colorless oil) in 80% yield.

Workup

  1. temperatureThe reaction solution was cooled in an ice bath
  2. customAfter removing the ice bath
  3. addition20 mL of saturated sodium bicarbonate solution were added
  4. extractionthe reaction solution was extracted with dichloromethane (20 mL×3)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography with elution system

Sources & evidence

ORD record
ord-73ad979d6f8041dcaf22d1de45a9be45
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

Loading…