Pyridine → HCID 59312242, compound

HRID 2077043Notes

Reaction equation

HRID 2077043 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH2:16]([C:23]1[NH:24][C:25](=O)[C:26]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28][C:27]=2[N:40]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:16]([C:23]1[N:24]=[C:25]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])[C:26]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:29][CH2:28][C:27]=2[N:40]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 135741926HCID 135741926, compound

Product 1

HCID 59312242HCID 59312242, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triflic anhydride (516 mg, 0.30 mL, 1.83 mmol) was added dropwise to a solution of the product of Step A (500 mg, 1.41 mmol) and pyridine (167 mg, 0.17 mL, 2.11 mmol) in CH2Cl2 (5.0 mL) at 0° C. The resulting solution was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was quenched by addition of water then partitioned between 5% citric acid and ethyl acetate. The organic layer was washed with sodium bicarbonate (sat.), dried over magnesium sulfate and concentrated under vacuum to yield the crude product as a yellow gum (670 mg). This material was taken on without further purification.

Workup

  1. customThe reaction mixture was quenched by addition of water
  2. customthen partitioned between 5% citric acid and ethyl acetate
  3. washThe organic layer was washed with sodium bicarbonate (sat.)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7adfcc3bbf8f49a89618c162c5779c8e
Source dataset
uspto-grants-2011_04
Patent number
US07928099B2

Reaction notes

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