Trifluoroacetic acid → 2-(3-((2-(cyclohex-1-en-1-yl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-cyclopropylacetamide

HRID 1051022Notes

Reaction equation

HRID 1051022 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([NH:25][CH:26]4[CH2:28][CH2:27]4)=[O:24])[CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:29][N:30](C)[C:31](=O)OC(C)(C)C)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[O:21][CH2:22][C:23]([NH:25][CH:26]3[CH2:27][CH2:28]3)=[O:24])(=[O:13])=[O:14])[CH:10]=[C:9]([CH2:29][NH:30][CH3:31])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90168922tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 901685852-(3-((2-(cyclohex-1-en-1-yl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-cyclopropylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(cyclopropylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7e (97 mg, 0.22 mmol) was dissolved in 8 mL of dichloromethane, and the reaction solution was cooled in an ice bath, followed by dropwise addition of 2 mL of trifluoroacetic acid. After removing the ice bath, the reaction solution was stirred at room temperature for 2 h. A saturated sodium bicarbonate solution was added dropwise until the pH of the reaction solution was 7 to 8, and then it 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 thin layer chromatography with elution system A to obtain the title product 2-(3-((2-(cyclohex-1-en-1-yl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-cyclopropylacetamide 7 (67 mg, a light yellow oil) in 85% yield.

Workup

  1. temperaturethe reaction solution was cooled in an ice bath
  2. customAfter removing the ice bath
  3. additionA saturated sodium bicarbonate solution was added dropwise until the pH of the reaction solution
  4. extractionit 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 thin layer chromatography with elution system

Sources & evidence

ORD record
ord-6a3742b97516407dae42aad50c38026b
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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