Hydrochloric Acid → 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N,N-dimethylacetamide

HRID 1051030Notes

Reaction equation

HRID 1051030 reaction equation
[CH3:1][N:2]([CH3:38])[C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([S:12]([N:15]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])=[CH:18][C:17]([CH2:27][N:28](C)[C:29](=O)OC(C)(C)C)=[CH:16]2)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1.Cl>ClCCl.O1CCOCC1>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]1[N:15]([S:12]([C:8]2[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=2)[O:5][CH2:4][C:3]([N:2]([CH3:1])[CH3:38])=[O:37])(=[O:14])=[O:13])[CH:16]=[C:17]([CH2:27][NH:28][CH3:29])[CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 90168924tert-butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 901686932-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N,N-dimethylacetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl ((1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-5-(2-fluorophenyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 9c (54 mg, 0.10 mmol) was dissolved in 4 mL of dichloromethane, and the reaction solution was cooled in an ice bath, followed by dropwise addition of a solution of hydrogen chloride in 1,4-dioxane (4 N, 4 mL). After removing the ice bath, the reaction solution was stirred at room temperature for 3h. A saturated sodium bicarbonate solution was added dropwise until the pH of the reaction solution was 7 to 8, 5 mL of water were added, and then the reaction solution was extracted with ethyl acetate (10 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the title product 2-(3-((2-(2-fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N,N-dimethylacetamide 9 (20 mg, a yellow solid) in 45% 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. additionwere added
  5. extractionthe reaction solution was extracted with ethyl acetate (10 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-276a26cad1c74f4f8898359c6a6445e4
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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