1,2-Diaminocyclohexane, trans- → 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester

HRID 80148Notes

Reaction equation

HRID 80148 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].[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21](Br)[CH:20]=[CH:19][C:18]=1[F:24].N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:14][O:15][C:16](=[O:25])[C:17]1[CH:22]=[C:21]([N:10]2[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]2=[O:13])[CH:20]=[CH:19][C:18]=1[F:24]

Participants

7

Reactant 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 21525435Methyl 5-bromo-2-fluorobenzoateHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 687859672-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl esterYield 88.8%

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: 315 mg, 1.78 mmol) was reacted with 5-bromo-2-fluoro-benzoic acid methyl ester (500 mg, 2.14 mmol), 1,4-dioxane (30 mL), copper iodide (34 mg, 0.178 mmol), trans-1,2-diamino cyclohexane (0.08 mL, 0.534 mmol) and potassium phosphate (935 mg, 4.45 mmol) to afford 520 mg of 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (88.8% yield).

Sources & evidence

ORD record
ord-a7af2d2eee5c40a8ab8a515195c409c5
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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