Methanol → HCID 59636237, compound

HRID 2383819Notes

Reaction equation

HRID 2383819 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[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17](S(C3C=CC(C)=CC=3)(=O)=O)[CH:16]=2)[C:11]1=[O:34].CO>C(O)C.C(Cl)(Cl)Cl>[NH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([N:12]2[CH2:13][CH2:14][N:10]([C:5]3[CH:6]=[N:7][CH:8]=[CH:9][C:4]=3[CH3:3])[C:11]2=[O:34])=[CH:16]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68784532HCID 68784532, compound

Product 1

HCID 59636237HCID 59636237, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

LCMS purity: 92.68%, m/z=446.9 (M+1) 10% NaOH solution (10 mL) was added to a solution of 1-(4-methyl-pyridin-3-yl)-3-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]-imidazolidin-2-one (110 mg, 0.0002 mol) in ethanol (10 mL) and the resulting mixture was stirred at 90° C. for 1 hour. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and ice water. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 50 mg of the product (86.2% yield).

Workup

  1. customThe reaction mixture was partitioned between ethylacetate and ice water
  2. washThe organic layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-6cd72b3ac7c04dbeb87fcb6657149986
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

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