Trifluoromethanesulfonic anhydride → HCID 18779739, compound

HRID 1421753Notes

Reaction equation

HRID 1421753 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][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:4]=1.[Cl:21][C:22]1[CH:23]=[CH:24][C:25](=[O:59])[N:26]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]3[N:36]=[CH:37][N:38](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:39]=3)=[CH:30][N:29]=2)[CH:27]=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:21][C:22]1[CH:23]=[CH:24][C:25](=[O:59])[N:26]([C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]3[N:36]([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][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)[CH:4]=4)[CH:37]=[N:38][CH:39]=3)=[CH:30][N:29]=2)[CH:27]=1

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 81531DiisopropylethylamineHCID 18779729HCID 18779729, compoundHCID 702869365-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one

Product 1

HCID 18779739HCID 18779739, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a cooled solution (-78° C.) of 4-hydroxymethyl-2-(3-phenyl-propoxy)-benzonitrile from step 3 (35 mg, 0.13 mmol) and 5-chloro-5'-(1-trityl-1H-imidazol-4-ylmethyl)-[1,2']bipyridinyl-2-one from Example 23, Step 5 (70 mg, 0.13 mmol) in CH2Cl2 (650 μl) was added DIEA (50 μl, 0.27 mmol) followed immediately by the addition of Tf2O (33 μl, 0.19 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 (650 μl) and heated to 60° C. for 14 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.

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 (650 μl)
  5. temperatureheated to 60° C. for 14 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)

Sources & evidence

ORD record
ord-8301d5ffd49242b9aa6cef1876e0c750
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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