Trifluoromethanesulfonic anhydride → HCID 18779722, compound

HRID 1585939Notes

Reaction equation

HRID 1585939 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15](=[O:49])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]3[N:26]=[CH:27][N:28](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:29]=3)=[CH:20][N:19]=2)[CH:17]=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:11][C:12]1[CH:13]=[CH:14][C:15](=[O:49])[N:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]3[N:26]([CH2:2][C:3]4[CH:4]=[CH:5][C:6]([C:9]#[N:10])=[N:7][CH:8]=4)[CH:27]=[N:28][CH:29]=3)=[CH:20][N:19]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 122519662-Cyano-5-hydroxymethylpyridineHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 18779722HCID 18779722, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of 5-hydroxymethyl-pyridine-2-carbonitrile from step 3 (37 mg, 0.28 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (150 mg, 0.28 mmol) in CH2Cl2 (1.38 ml) was added DIEA (106 μl, 0.61 mmol) followed immediately by the addition of Tf2O (70 μl, 0.41 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 (1.38 ml) and heated to 60° C. for several hours. The MeOH was removed in vacuo and the residue treated with saturated NaHCO3 (2 mL) and extracted with CH2Cl2 (2×10 mL). The organic layer was washed with brine (1×10 mL), dried (MgSO4), filtered and concentrated. 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 (1.38 ml)
  5. temperatureheated to 60° C. for several hours
  6. customThe MeOH was removed in vacuo
  7. additionthe residue treated with saturated NaHCO3 (2 mL)
  8. extractionextracted with CH2Cl2 (2×10 mL)
  9. washThe organic layer was washed with brine (1×10 mL)
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customResidue was purified by flash chromatography [4% MeOH(5% NH4OH)/CH2Cl2 ]

Sources & evidence

ORD record
ord-513181e1dd4040e4871d96f19c7f3a7b
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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