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 587786ノート

反応式

HRID 587786 の反応式
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]

参加物

6

反応物 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

生成物 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)benzamide収率 52%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-14bf7db4aa4e4a2ea5ab2acafe55d829
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

反応ノート

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