1,2-Diaminocyclohexane, trans- → 1-Benzothiazol-6-yl-3-[4-(1-hydroxyethyl)-pyridin-3-yl]-imidazolidin-2-one

HRID 80204Notes

Reaction equation

HRID 80204 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[CH:23]([OH:25])[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[CH:23]([OH:25])[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 666785541-Benzothiazol-6-yl-imidazolidin-2-oneHCID 667978531-(3-Bromopyridin-4-yl)ethanol

Product 1

HCID 498724581-Benzothiazol-6-yl-3-[4-(1-hydroxyethyl)-pyridin-3-yl]-imidazolidin-2-oneYield 3.9%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as described in example 14, 1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 150 mg, 0.6849 mmol) was reacted with 1-(3-bromo-pyridin-4-yl)-ethanol (137.6 mg, 0.6849 mmol), 1,4-dioxane (5 mL), copper iodide (13.04 mg, 0.06849 mmol), trans-1,2-diamino cyclohexane (23.52 mg, 0.205 mmol) and potassium phosphate (435.1 mg, 2.05 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3), followed by preparative HPLC afforded 9 mg of the product (3.9% yield).

Workup

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

Sources & evidence

ORD record
ord-46e2617ce84a4a1d991cadfff03ee830
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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