8-Bromoquinoline → 2-cyclohexyl-8-((E)-2-quinolin-8-yl-ethenesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one

HRID 1755001노트

반응식

HRID 1755001 반응식
[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18]([CH:21]=[CH2:22])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:24]1[CH:25]=[CH:26][CH:27]=[C:28]2[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]2.C([O-])(=O)C.[Na+]>CC(N(C)C)=O>[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18](/[CH:21]=[CH:22]/[C:24]4[CH:25]=[CH:26][CH:27]=[C:28]5[C:33]=4[N:32]=[CH:31][CH:30]=[CH:29]5)(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 3

HCID 1401098-BromoquinolineHCID 517045Sodium AcetateHCID 668163772-Cyclohexyl-8-ethenesulfonyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one

생성물 1

HCID 668174242-cyclohexyl-8-((E)-2-quinolin-8-yl-ethenesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one수율 55%

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

실험 절차

2-Cyclohexyl-8-ethenesulfonyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (20 mg, 61.5 μmol), 8-bromoquinoline (19 mg, 91.3 μmol), POPd1 (Combiphos, 2.9 mg, 3.1 μmol) and sodium acetate (7.6 mg, 92.6 μmol) in dimethylacetamide (0.6 ml) were mixed in a sealed vessel in a nitrogen atmosphere. This mixture was irradiated in a microwave apparatus (190° C., 40 min). The reaction mixture was cooled, and then quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2-cyclohexyl-8-((E)-2-quinolin-8-yl-ethenesulfonyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (15.3 mg, 16%).

후처리

  1. customThis mixture was irradiated in a microwave apparatus (190° C., 40 min)
  2. temperatureThe reaction mixture was cooled
  3. customquenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-cbd0fcf1954a4f1b9bc533ed50b20aaa
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

반응 노트

불러오는 중…