Trifluoromethanesulfonic anhydride → 1-(2-(Thien-2-yl) pyrid-5-ylmethyl)-5-(4-cyanobenzyl)imidazole

HRID 1004609노트

반응식

HRID 1004609 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][N:7]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([N:57]1[CH:61]=[C:60]([CH2:62][C:63]2[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=2)[N:59]=[CH:58]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:59]2[C:60]([CH2:62][C:63]3[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=3)=[CH:61][N:57]=[CH:58]2)=[CH:8][N:7]=1

참가 물질

6

반응물 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 15411145(6-Thien-2-ylpyrid-3-yl)methanolHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazole

생성물 1

HCID 99067091-(2-(Thien-2-yl) pyrid-5-ylmethyl)-5-(4-cyanobenzyl)imidazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of 2-(thien-2-yl)-5-hydroxymethylpyridine (255 mg, 1.33 mmol) and diisopropylethylamine (0.464 mL, 2.66 mmol) in dichloromethane (7 mL) at -78° C. is added trifluoromethane-sulfonic anhydride (0.224 mL, 1.33 mmol) and the mixture stirred at -78° C. for 1 hour. To this mixture is added a solution of 1-trityl-4-(4-cyanobenzyl)-imidazole (566 mg, 1.33 mmol) in dichloromethane (5 mL). The mixture is allowed to warm to ambient temperature and stirred for 2 hours. The solvent is evaporated in vacuo. The residue is dissolved in methanol (50 mL), heated at reflux for 1 hour, and the solvent is evaporated in vacuo. The residue is partitioned between dichloromethane and sat. aq. NaHCO3 solution. The organic layer is dried, (Na2SO4) and the solvent evaporated in vacuo. The residue is chromatographed to afford the title compound.

후처리

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 2 hours
  3. customThe solvent is evaporated in vacuo
  4. dissolutionThe residue is dissolved in methanol (50 mL)
  5. temperatureheated
  6. temperatureat reflux for 1 hour
  7. customthe solvent is evaporated in vacuo
  8. customThe residue is partitioned between dichloromethane and sat. aq. NaHCO3 solution
  9. customThe organic layer is dried
  10. custom(Na2SO4) and the solvent evaporated in vacuo
  11. customThe residue is chromatographed

출처 및 근거

ORD 기록
ord-5b3a06f6457c4b0e8c20554a4c520f32
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051574

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