Potassium Carbonate → HCID 117987758, compound

HRID 2206085Notes

Reaction equation

HRID 2206085 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:17])[C:8]1[C:13](I)=[CH:12][CH:11]=[N:10][C:9]=1[O:15][CH3:16])([CH3:4])([CH3:3])[CH3:2].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:1]([N:5]1[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:15][CH3:16])[C:8]=2[C:7](=[O:17])[NH:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 117988190HCID 117988190, compound

Product 1

HCID 117987758HCID 117987758, compoundYield 53.8%

Reagents, catalysts & solvents 2

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

Procedure

A solution of N′-tert-butyl-4-iodo-2-methoxynicotinohydrazide (1.00 g), L-proline (0.066 g), potassium carbonate (0.792 g) and copper(I) iodide (0.055 g) in DMSO (30 mL) was stirred under nitrogen atmosphere at room temperature for 6 hr. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (341 mg).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5a406fda110a445ebb813afb281a8a18
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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