Methanol → 1-(1H-indol-6-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-one

HRID 80186Notes

Reaction equation

HRID 80186 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[N:10]1[CH2:14][CH2:13][N:12]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][N:21]3S(C3C=CC(C)=CC=3)(=O)=O)=[CH:17][CH:16]=2)[C:11]1=[O:34].CO>C(O)C.C(Cl)(Cl)Cl>[NH:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([N:12]3[CH2:13][CH2:14][N:10]([C:5]4[CH:6]=[N:7][CH:8]=[CH:9][C:4]=4[CH3:3])[C:11]3=[O:34])[CH:23]=2)[CH:19]=[CH:20]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68788691HCID 68788691, compound

Product 1

HCID 596362581-(1H-indol-6-yl)-3-(4-methylpyridin-3-yl)imidazolidin-2-oneYield 47.54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

10% NaOH solution (10 mL) was added to a solution of 1-(4-methyl-pyridin-3-yl)-3-[1-(toluene-4-sulfonyl)-1H-indol-6-yl]-imidazolidin-2-one (I-144a: 94 mg) in ethanol (10 mL). The resulting mixture was heated to reflux at 90° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer was washed with water, brine solution, dried and concentrated. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 29 mg of the product (47.54% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethylacetate and water
  4. washThe organic layer was washed with water, brine solution
  5. customdried
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (2% MeOH in DCM)

Sources & evidence

ORD record
ord-442751f32dbd4d7fb46db52b50515535
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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