Trifluoroacetic acid → 2-(3-((2-(2-Fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide

HRID 1051005노트

반응식

HRID 1051005 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]([NH:26][CH3:27])=[O:25])[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:28][N:29](C)[C:30](=O)OC(C)(C)C)[CH:9]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=2)[O:22][CH2:23][C:24]([NH:26][CH3:27])=[O:25])(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:28][NH:29][CH3:30])[CH:9]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 90168692tert-butyl ((5-(2-fluorophenyl)-1-((3-(2-(methylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

생성물 1

HCID 738909672-(3-((2-(2-Fluorophenyl)-4-((methylamino)methyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)-N-methylacetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-Butyl ((5-(2-fluorophenyl)-1-((3-(2-(methylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 1j (60 mg, 0.11 mmol) was dissolved in 8 mL of dichloromethane, followed by addition of 2 mL of trifluoracetic acid, and then the reaction solution was stirred for 1 h. 20 mL of saturated sodium bicarbonate solution was added, and the reaction solution was extracted with dichloromethane (30 mL×2). 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)-N-methylacetamide 1 (15 mg, a yellow oil), and the yield of the three steps was 16%.

후처리

  1. extractionthe reaction solution was extracted with dichloromethane (30 mL×2)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography with elution system

출처 및 근거

ORD 기록
ord-929dcb5052844ad09aa269e24b602e97
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388133B2

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