Trifluoromethanesulfonic anhydride → HCID 18779702, 화합물

HRID 1421750노트

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HRID 1421750 반응식
O[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:4]=1.[Cl:22][C:23]1[CH:24]=[CH:25][C:26](=[O:60])[N:27]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]3[N:37]=[CH:38][N:39](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:40]=3)=[CH:31][N:30]=2)[CH:28]=1.CCN(C(C)C)C(C)C.O(S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O>C(Cl)Cl>[Cl:22][C:23]1[CH:24]=[CH:25][C:26](=[O:60])[N:27]([C:29]2[CH:34]=[CH:33][C:32]([CH2:35][C:36]3[N:37]([CH2:2][C:3]4[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=5)[CH:4]=4)[CH:38]=[N:39][CH:40]=3)=[CH:31][N:30]=2)[CH:28]=1

참가 물질

6

반응물 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 18779759HCID 18779759, 화합물HCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

생성물 1

HCID 18779702HCID 18779702, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

To a cooled solution (-78° C.) of 4-hydroxymethyl-2-(4-phenyl-butoxy)-benzonitrile from step 2 (100 mg, 0.36 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23 Step 5 (188 mg, 0.36 mmol) in CH2Cl2 (2 ml) was added DIEA (136 μl, 0.78 mmol) followed immediately by the addition of Tf2O (90 μl, 0.53 mmol). The reaction mixture stirred at -78° C. for 1 hour and was then transferred to an ice bath and stirred at 0° C. for another hour. The solvent was removed in vacuo. The residue was then dissolved in MeOH (2 ml) and heated to 60° C. for several hours. The MeOH was then removed in vacuo and the residue treated with saturated NaHCO3 (5 mL) and extracted with CH2Cl2 (2×10 mL). The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2) to yield the final product.

후처리

  1. customwas then transferred to an ice bath
  2. stirringstirred at 0° C. for another hour
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was then dissolved in MeOH (2 ml)
  5. temperatureheated to 60° C. for several hours
  6. customThe MeOH was then removed in vacuo
  7. additionthe residue treated with saturated NaHCO3 (5 mL)
  8. extractionextracted with CH2Cl2 (2×10 mL)
  9. washThe organic layer was washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe residue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2)

출처 및 근거

ORD 기록
ord-83d78d0ebc7946c5b81e9da8e0033f0c
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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