Pyridine → HCID 66817658, compound

HRID 1755031Notes

Reaction equation

HRID 1755031 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:14]([O:18][C:19]([N:21]1[CH2:40][CH2:39][C:24]2([N:28]=[C:27]([C:29]3[CH:34]=[CH:33][C:32]([C:35](=O)[NH2:36])=[CH:31][CH:30]=3)[NH:26][C:25]2=[O:38])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[C:14]([O:18][C:19]([N:21]1[CH2:22][CH2:23][C:24]2([N:28]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([C:35]#[N:36])=[CH:33][CH:34]=3)[NH:26][C:25]2=[O:38])[CH2:39][CH2:40]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 66817711HCID 66817711, compound

Product 1

HCID 66817658HCID 66817658, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Trifluoroacetic anhydride (0.287 ml, 2.07 mmol) was added to a solution of 2-(4-carbamoyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (350 mg, 0.94 mmol) and pyridine (0.303 ml) in dioxane (1.1 ml) at 0° C. The mixture was stirred for 30 minutes and then stirred at room temperature for one hour. An aqueous NaHCO3 solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give 2-(4-cyano-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester as a white powder (235 mg, 71%).

Workup

  1. stirringstirred at room temperature for one hour
  2. extractionfollowed by extraction with dichloromethane
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-6e221216c31f42d1af0da3a7e5931de8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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