Water → HCID 117987863, compound

HRID 2205989Notes

Reaction equation

HRID 2205989 reaction equation
[CH:1]1([NH:6][NH:7][C:8](=[O:18])[C:9]2[C:14](I)=[CH:13][CH:12]=[N:11][C:10]=2[O:16][CH3:17])[CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.[Cu]I>[CH:1]1([N:6]2[C:14]3[CH:13]=[CH:12][N:11]=[C:10]([O:16][CH3:17])[C:9]=3[C:8](=[O:18])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 117987881HCID 117987881, compound

Product 1

HCID 117987863HCID 117987863, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of N′-cyclopentyl-4-iodo-2-methoxynicotinohydrazide (695 mg), L-proline (44.3 mg), potassium carbonate (532 mg) and copper(I) iodide (36.6 mg) in DMSO (18 mL) was stirred under nitrogen atmosphere at room temperature for 5 hr. To the reaction mixture was added water under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was removed, to the obtained aqueous layer was added 1N hydrochloric acid (7 mL) under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (174 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was removed, to the obtained aqueous layer
  4. additionwas added 1N hydrochloric acid (7 mL) under ice-
  5. temperaturecooling
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-05ae51e4c7ce46ccb65f8c747970de2d
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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