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

HRID 1051007Notes

Reaction equation

HRID 1051007 reaction equation
[NH2:1][C:2](=[O:36])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([S:11]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[CH:17][C:16]([CH2:26][N:27](C)[C:28](=O)OC(C)(C)C)=[CH:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[N:14]([S:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[O:4][CH2:3][C:2]([NH2:1])=[O:36])(=[O:12])=[O:13])[CH:15]=[C:16]([CH2:26][NH:27][CH3:28])[CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90168683tert-butyl ((1-((3-(2-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 747629962-(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-amino-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 2a (100 mg, 0.19 mmol) was dissolved in 20 mL of dichloromethane. The reaction solution was cooled in an ice bath, 5 mL of trifluoroacetic acid were dropwise added, and then the reaction solution was stirred for 2 h. 50 mL of saturated sodium bicarbonate solution were added, and the reaction solution was extracted with dichloromethane (50 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 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetamide 2 (60 mg, a yellow oil) in 75% yield.

Workup

  1. temperatureThe reaction solution was cooled in an ice bath
  2. extractionthe reaction solution was extracted with dichloromethane (50 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system

Sources & evidence

ORD record
ord-6208d864d3234a7a9ea9826fc7aaa1fb
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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