Cesium carbonate → N-{1-[4-(Isoquinolin-3-ylamino)-benzenesulfonyl]-piperidin-4-yl}-acrylamide

HRID 337237ノート

反応式

HRID 337237 の反応式
C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:50]1[CH:59]=[CH:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[N:51]=1.[NH2:60][C:61]1[CH:66]=[CH:65][C:64]([S:67]([N:70]2[CH2:75][CH2:74][CH:73]([NH:76][C:77](=[O:80])[CH:78]=[CH2:79])[CH2:72][CH2:71]2)(=[O:69])=[O:68])=[CH:63][CH:62]=1>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:52]1[C:57]2[C:58](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:59]=[C:50]([NH:60][C:61]2[CH:62]=[CH:63][C:64]([S:67]([N:70]3[CH2:71][CH2:72][CH:73]([NH:76][C:77](=[O:80])[CH:78]=[CH2:79])[CH2:74][CH2:75]3)(=[O:68])=[O:69])=[CH:65][CH:66]=2)[N:51]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 119282-ChloroquinolineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 71618273N-[1-(4-Amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide

生成物 1

HCID 86674091N-{1-[4-(Isoquinolin-3-ylamino)-benzenesulfonyl]-piperidin-4-yl}-acrylamide収率 0.5%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Tris(dibenzylideneacetone)dipalladium (0) (0.05 g, 0.06 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.015 g, 0.03 mmol), cesium carbonate (0.5 g, 2.0 mmol) and 2-chloroquinoline (0.085 g, 0.52 mmol) were added sequentially to a stirred solution of N-[1-(4-amino-benzenesulfonyl)-piperidin-4-yl]-acrylamide in dry dioxane (5 ml) under a nitrogen atmosphere. The mixture was heated to 110° C. for 12 hours. After this time the mixture was cooled to room temperature, filtered through a pad of celite, the celite was washed with EtOAc (50 ml) and the filtrate was washed sequentially with citric acid (10% solution, 20 ml) and brine (20 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated. The resulting residue was purified by prep HPLC to give the title compound (0.002 g, 0.5% yield) as a white solid.

後処理

  1. temperatureAfter this time the mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with EtOAc (50 ml)
  4. washthe filtrate was washed sequentially with citric acid (10% solution, 20 ml) and brine (20 ml)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by prep HPLC

出典と根拠

ORDレコード
ord-5a056d78a55a45b3951f9735550cfac0
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

読み込み中…