1,2-Diaminocyclohexane, trans- → HCID 49872553, compound

HRID 80196Notes

Reaction equation

HRID 80196 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([Cl:24])[C:22]=1[CH3:23].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([Cl:24])[C:22]=4[CH3:23])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-oneHCID 687843183-Bromo-5-chloro-4-methylpyridine

Product 1

HCID 49872553HCID 49872553, compoundYield 34.21%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 100 mg, 0.456 mmol) was reacted with 3-bromo-5-chloro-4-methyl-pyridine (94 mg, 0.456 mmol), 1,4-dioxane (5 mL), copper iodide (8.68 mg, 0.0456 mmol), trans-1,2-diamino cyclohexane (15.66 mg, 0.1368 mmol) and potassium phosphate (290.38 mg, 1.368 mmol) to afford the crude product. Purification by preparative HPLC afforded 52 mg of the product (34.21% yield).

Workup

  1. customto afford the crude product
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-4608fdf55184466ca8aca0b85d518e78
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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