1,2-Diaminocyclohexane, trans- → HCID 59636224, compound

HRID 80132

Reaction equation

HRID 80132 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].I[C:15]1[CH:24]=[CH:23][C:18]2[N:19]=[C:20]([CH3:22])[S:21][C:17]=2[CH:16]=1.N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:22][C:20]1[S:21][C:17]2[CH:16]=[C:15]([N:10]3[CH2:11][CH2:12][N:8]([C:3]4[CH:4]=[N:5][CH:6]=[CH:7][C:2]=4[CH3:1])[C:9]3=[O:13])[CH:24]=[CH:23][C:18]=2[N:19]=1

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 8075926-Iodo-2-methyl-1,3-benzothiazoleHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 59636224HCID 59636224, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 100 mg, 0.5643 mmol) was reacted with 6-iodo-2-methyl-benzothiazole (154 mg, 0.5598 mmol), 1,4-dioxane (20 mL), copper iodide (10.7 mg, 0.056 mmol), trans-1,2-diamino cyclohexane (19.4 mg, 0.169 mmol) and potassium phosphate (300 mg, 1.413 mmol) to afford the crude product. Purification by column chromatography on silica gel (5% MeOH in CHCl3) afforded 115 mg of the product (62.8% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-9a5c7c42ad47418187027b444f88a9d4
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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