Trifluoromethanesulfonic anhydride → HCID 18779760, compound

HRID 1421747Notes

Reaction equation

HRID 1421747 reaction equation
O[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:4]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24](=[O:58])[N:25]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34]3[N:35]=[CH:36][N:37](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:38]=3)=[CH:29][N:28]=2)[CH:26]=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:20][C:21]1[CH:22]=[CH:23][C:24](=[O:58])[N:25]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][C:34]3[N:35]([CH2:2][C:3]4[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([O:11][CH2:12][CH2:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[CH:4]=4)[CH:36]=[N:37][CH:38]=3)=[CH:29][N:28]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 18779715HCID 18779715, compoundHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 18779760HCID 18779760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of 4-hydroxymethyl-2-phenethyloxy-benzonitrile from step 2 (65 mg, 0.26 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23 Step 5 (136 mg, 0.26 mmol) in CH2Cl2 (2 ml) was added DIEA (100 μl, 0.56 mmol) followed immediately by the addition of Tf2O (65 μl, 0.39 mmol). The reaction mixture was 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 aqueous 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.

Workup

  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 aqueous 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 ]

Sources & evidence

ORD record
ord-cc300c04677f4488badc29449d0473a5
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

Loading…