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

HRID 1051030노트

반응식

HRID 1051030 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-276a26cad1c74f4f8898359c6a6445e4
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388133B2

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