Potassium Carbonate → HCID 59636157, compound

HRID 80107

Reaction equation

HRID 80107 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[N:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16].Br[C:18]1[CH:19]=[N:20][CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:25][O:24][C:22]1[CH:23]=[C:18]([N:13]2[CH2:14][CH2:15][N:11]([C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[C:12]2=[O:16])[CH:19]=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 8171633-Bromo-5-methoxypyridineHCID 596361671-Naphthalen-2-yl-imidazolidin-2-one

Product 1

HCID 59636157HCID 59636157, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 79, 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 112.7 mg, 0.5319 mmol) was reacted with 3-bromo-5-methoxy-pyridine (100 mg, 0.5319 mmol), 1,4-dioxane (5 mL), copper iodide (10.13 mg, 0.05319 mmol), trans-1,2-diamino cyclohexane (18.27 mg, 0.1595 mmol) and potassium carbonate (147.07 mg, 1.0638 mmol) to afford the crude product. Purification by column chromatography on silica gel (30% EtOAc in hexane) afforded 48 mg of the product (30.3% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (30% EtOAc in hexane)

Sources & evidence

ORD record
ord-ce0b89e1e5894ce3a20c362243653f43
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

Loading…