Potassium Phosphate, Tribasic → 1-Benzothiazol-6-yl-4,5-dimethyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80233Notes

Reaction equation

HRID 80233 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]([CH3:15])[CH:13]([CH3:16])[NH:12][C:11]3=[O:17])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[CH3:25].CN(C)C1CCCCC1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.C(OCC)(=O)C.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH:14]([CH3:15])[CH:13]([CH3:16])[N:12]([C:19]4[CH:20]=[N:21][CH:22]=[CH:23][C:24]=4[CH3:25])[C:11]3=[O:17])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 12447266N1,N1-dimethylcyclohexane-1,2-diamineHCID 144235133-Iodo-4-methylpyridineHCID 596362571-Benzothiazol-6-yl-4,5-dimethyl-imidazolidin-2-one

Product 1

HCID 498726501-Benzothiazol-6-yl-4,5-dimethyl-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 8.8%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-4,5-dimethyl-imidazolidin-2-one (I-175b: 50 mg, 0.202 mmol) was refluxed with 3-iodo-4-methyl-pyridine (44.33 mg, 0.202 mmol), copper iodide (3.85 mg, 0.0202 mmol), N,N-dimethyl-cyclohexane-1,2-diamine (0.0095 mL, 0.061 mmol), potassium phosphate (107.2 mg, 0.506 mmol) and 1,4-dioxane (5 mL) at 120° C. for 16 hours to afford the crude product. The reaction was monitored by TLC (100% ethyl acetate). Purification by column chromatography on silica gel (60% ethyl acetate in hexane) followed by preparative HPLC afforded 6 mg of the product (8.76% yield).

Workup

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-830e02aba2004bf4b6fdf16146e3d15b
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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