Diisopropylethylamine → (E)-2-Bromo-4-(3-(3,5-dichloro-4-hydroxyphenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide

HRID 587786노트

반응식

HRID 587786 반응식
CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH2:43][CH2:44][C:45]([NH:47][CH2:48][C:49]([F:52])([F:51])[F:50])=[O:46].[Br:53][C:54]1[CH:62]=[C:61](/[CH:63]=[CH:64]/[CH:65]([C:70]2[CH:75]=[C:74]([Cl:76])[C:73]([OH:77])=[C:72]([Cl:78])[CH:71]=2)[C:66]([F:69])([F:68])[F:67])[CH:60]=[CH:59][C:55]=1[C:56](O)=[O:57]>C(Cl)Cl>[Br:53][C:54]1[CH:62]=[C:61](/[CH:63]=[CH:64]/[CH:65]([C:70]2[CH:71]=[C:72]([Cl:78])[C:73]([OH:77])=[C:74]([Cl:76])[CH:75]=2)[C:66]([F:69])([F:68])[F:67])[CH:60]=[CH:59][C:55]=1[C:56]([NH:43][CH2:44][C:45](=[O:46])[NH:47][CH2:48][C:49]([F:52])([F:51])[F:50])=[O:57]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 86722767(E)-2-bromo-4-(3-(3,5-dichloro-4-hydroxyphenyl)-4,4,4-trifluorobut-1-enyl)benzoic acid

생성물 1

HCID 86722766(E)-2-Bromo-4-(3-(3,5-dichloro-4-hydroxyphenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

DIPEA (0.20 mL, 1.26 mmol), PyBOP (245 mg, 0.47 mmol) and 2-amino-N-(2,2,2-trifluoroethyl)acetamide (90 mg, 0.47 mmol) were added to a stirred solution of (E)-2-bromo-4-(3-(3,5-dichloro-4-hydroxyphenyl)-4,4,4-trifluorobut-1-enyl)benzoic acid (200 mg, 0.42 mmol, 66% purity) in CH2Cl2 (5 mL) at ambient temperature. The resulting mixture was then stirred for 12 h. The reaction mixture was diluted with CH2Cl2, washed with 1N HCl, followed by saturated sodium bicarbonate solution, brine solution and water. The organic layer was dried (Na2SO4), filtered, concentrated under vacuum. The residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% EtOAc in petroleum ether to give the title compound as light green solid (130 mg, 52%).

후처리

  1. washwashed with 1N HCl
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica (100-200 mesh)
  6. washeluting with 30% EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-14bf7db4aa4e4a2ea5ab2acafe55d829
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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