1,2-Diaminocyclohexane, trans- → 1-Benzothiazol-6-yl-3-(4-methyl-5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one Trifluoro-acetic Acid

HRID 2383943Notes

Reaction equation

HRID 2383943 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]([C:24]([F:27])([F:26])[F:25])[C:22]=1[CH3:23].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=[O:37].[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[F:25][C:24]([F:27])([F:26])[C:11]([OH:15])=[O:37].[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]([C:24]([F:26])([F:27])[F:25])[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 596361753-Bromo-4-methyl-5-(trifluoromethyl)pyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 866494011-Benzothiazol-6-yl-3-(4-methyl-5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one Trifluoro-acetic AcidYield 3.6%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

1-Benzothiazol-6-yl-imidazolidin-2-one (I-84b: 80 mg, 0.365 mmol) was reacted with 3-bromo-4-methyl-5-trifluoromethyl-pyridine (I-189a: 90 mg, 0.365 mmol), 1,4-dioxane (5 mL), copper iodide (6.95 mg, 0.0365 mmol), trans-1,2-diamino cyclohexane (12.5 mg, 0.1095 mmol) and potassium phosphate (232.4 mg, 1.095 mmol) to afford the crude product. Purification by preparative HPLC afforded Sing of the product (3.6% yield).

Workup

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

Sources & evidence

ORD record
ord-6b0c8961d6064e658b6f2139b8c9d6bf
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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