Trifluoromethanesulfonic anhydride → 5-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-furan-2-carbonitrile

HRID 1585891

반응식

HRID 1585891 반응식
O[CH2:2][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14](=[O:48])[N:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[N:25]=[CH:26][N:27](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:28]=3)=[CH:19][N:18]=2)[CH:16]=1.C(N(C(C)C)CC)(C)C.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O>ClCCl>[Cl:10][C:11]1[CH:12]=[CH:13][C:14](=[O:48])[N:15]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[N:25]([CH2:2][C:3]4[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=4)[CH:26]=[N:27][CH:28]=3)=[CH:19][N:18]=2)[CH:16]=1

참가 물질

6

반응물 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 30214065-(Hydroxymethyl)furan-2-carbonitrileHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

생성물 1

HCID 187797255-[5-(5-chloro-2-oxo-2H-[1,2']bipyridinyl-5'-ylmethyl)-imidazol-1-ylmethyl]-furan-2-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

To a solution of the alcohol from step 2 (0.017 g, 0.137 mmol), 5-chloro-5'-(1-triphenylmethyl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (0.0758 g, 0.143 mmol) and diisopropylethylamine (0.047 mL, 1.49 mmol) in dichloromethane (1.3 mL) at -78° C. was added trifluoromethanesulfonic anhydride (0.023 mL, 0.136 mmol) and the mixture stirred at -78° C. for 1 hour. The mixture was allowed to warm to 0° C. and stirred for 2 hours. The solvent was evaporated in vacuo. The residue was dissolved in methanol (1 mL), heated at reflux for 2 hour, and the solvent evaporated in vacuo. The residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The organic layer was dried, (Na2SO4) and the solvent evaporated in vacuo. The residue was chromatographed (Silica gel, 1:99 to 3:97 MeOH:CH2Cl2) to afford the title compound as a white solid.

후처리

  1. temperatureto warm to 0° C.
  2. stirringstirred for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. dissolutionThe residue was dissolved in methanol (1 mL)
  5. temperatureheated
  6. temperatureat reflux for 2 hour
  7. customthe solvent evaporated in vacuo
  8. customThe residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  9. customThe organic layer was dried
  10. custom(Na2SO4) and the solvent evaporated in vacuo
  11. customThe residue was chromatographed (Silica gel, 1:99 to 3:97 MeOH:CH2Cl2)

출처 및 근거

ORD 기록
ord-5be46f66b328438a8c9b961110c2a306
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05939439

연결된 노트

불러오는 중…