1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-Methyl-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzamide

HRID 2383754Notes

Reaction equation

HRID 2383754 reaction equation
C[CH2:2][N:3]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.CN.[CH3:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][C:36]=1[N:41]1[CH2:45][CH2:44][N:43]([C:46]2[CH:54]=[CH:53][C:49]([C:50]([OH:52])=O)=[CH:48][CH:47]=2)[C:42]1=[O:55]>CN(C=O)C>[CH3:2][NH:3][C:50](=[O:52])[C:49]1[CH:48]=[CH:47][C:46]([N:43]2[CH2:44][CH2:45][N:41]([C:36]3[CH:37]=[N:38][CH:39]=[CH:40][C:35]=3[CH3:34])[C:42]2=[O:55])=[CH:54][CH:53]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 68784637HCID 68784637, compound

Product 1

HCID 59636255N-Methyl-4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzamideYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDCI (176.4 mg, 0.9205 mmol), HOBt (5.8 mg, 0.2525 mmol), DIPEA (0.3 mL, 2.3006 mmol) and methylamine hydrochloride (62 mg, 0.9205 mmol) were added to a stirred solution of 4-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid (228 mg, 0.7668 mmol) in dry DMF (10 mL) at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was partitioned between water and ethylacetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (5% MeOH in DCM) afforded 155 mg of the product (65.4% yield).

Workup

  1. customThe reaction mixture was partitioned between water and ethylacetate
  2. washThe organic layer was washed with water, brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography on silica gel (5% MeOH in DCM)

Sources & evidence

ORD record
ord-3e5863201bc34226ae9d92534d90ed5f
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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