1,2-Diaminocyclohexane, trans- → HCID 49872457, compound

HRID 80262Notes

Reaction equation

HRID 80262 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]=[CH:21][C:22]=1[CH2:23][CH3:24].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]=[CH:21][C:22]=4[CH2:23][CH3:24])[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 131605333-Bromo-4-ethylpyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 49872457HCID 49872457, compoundYield 3.75%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 600 mg, 2.739 mmol) was reacted with 3-bromo-4-ethyl-pyridine (512 mg, 2.739 mmol), 1,4-dioxane (10 mL), copper iodide (52 mg, 0.2739 mmol), trans-1,2-diamino cyclohexane (94.08 mg, 0.82 mmol) and potassium phosphate (1.74 mg, 8.2 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by preparative HPLC afforded 30 mg of the product (3.75% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-3e46c817caf741e9a2fde2dfc4c3c196
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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