Imidazole → HCID 86664547, compound

HRID 513281Notes

Reaction equation

HRID 513281 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15](I)[CH:14]=2)[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[N:20]1([C:15]2[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=2)[CH2:12][NH:11][C:9]2[C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=[C:2]([Cl:1])[CH:10]=2)[CH:24]=[CH:23][N:22]=[CH:21]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 866645466-Chloro-4-(3-iodobenzylamino)nicotinamide

Product 1

HCID 86664547HCID 86664547, compoundYield 51%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 6-chloro-4-(3-iodobenzylamino)nicotinamide (130 mg, 0.335 mmol), imidazole (30 mg, 0.441 mmol), 8-hydroxyquinoline (15 mg, 0.103 mmol), K2CO3 (60 mg, 0.434 mmol) and CuI (15 mg, 0.078 mmol) in DMSO (1 mL) was degassed with Ar, then was stirred at 130 C for 2 h. The mixture was purified by HPLC to give 4-(3-(1H-imidazol-1-yl)benzylamino)-6-chloronicotinamide (56 mg).

Workup

  1. customwas degassed with Ar
  2. customThe mixture was purified by HPLC

Sources & evidence

ORD record
ord-864fd7f4707248a592d9d5574e4af434
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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