Benzenesulfonamide, 3-amino- → 2-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamide

HRID 79093

반응식

HRID 79093 반응식
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:26][C:27]1[CH:28]=[C:29]([S:33]([NH2:36])(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>C(Cl)Cl.N1C=CC=CC=1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:15]=[C:14]([C:16]([CH3:17])([CH3:18])[CH3:19])[CH:13]=[CH:12][C:8]=2[C:9]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([S:33]([NH2:36])(=[O:34])=[O:35])[CH:28]=2)=[O:11])=[CH:20][CH:21]=1

참가 물질

7

반응물 3

HCID 7377Benzenesulfonamide, 3-amino-HCID 24386Thionyl ChlorideHCID 589880892-(4-Fluorophenoxy)-4-tert-butylbenzoic acid

생성물 1

HCID 248552112-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamide수율 50%

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

A solution of 2-(4-fluorophenoxy)-4-tert-butylbenzoic acid (0.11 g, 0.39 mmol) and thionyl chloride (0.28 mL, 3.9 mmol) in CH2Cl2 (10 mL) was stirred at room temperature for 4 h. The solvent was evaporated under reduced pressure, and to the resulting oil was added a solution of 3-amino-benzenesulfonamide (73 mg, 0.42 mmol) in pyridine (4 mL). The solution was stirred at room temperature 15 h. The reaction was diluted with water and extracted with EtOAc. The combined extracts were washed with water, dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes) to obtain a white solid which was recrystallized from EtOAc and hexanes. 2-(4-Fluorophenoxy)-4-tert-butyl-N-(3-(aminosulfonyl)phenyl)benzamide (85 mg, 50% yield) was obtained as a white solid. LC/MS: m/z 443.3 (M+H)+ at 3.49 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0%-50% EtOAc-hexanes)
  7. customto obtain a white solid which
  8. customwas recrystallized from EtOAc and hexanes

출처 및 근거

ORD 기록
ord-9f3311df790543d0b65bf661b6c85066
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841483B2

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