HCID 59485596, compound → HCID 59485920, compound

HRID 1972263Notes

Reaction equation

HRID 1972263 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]CC5C=CC=CC=5)[CH:19]=4)[CH2:16][N:15]([CH2:32][CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:14]3=[O:38])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1>CO.C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[CH2:16][N:15]([CH2:32][CH2:33][S:34]([CH3:37])(=[O:35])=[O:36])[C:14]3=[O:38])=[CH:11][CH:12]=2)=[CH:39][CH:40]=1

Participants

4

Reactant 1

HCID 59485596HCID 59485596, compound

Product 1

HCID 59485920HCID 59485920, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To 3-(4-(4-chlorophenoxy)phenyl)-4-(3-(benzyloxy)phenyl)-1-(2-(methylsulfonyl)ethyl)imidazolidin-2-one (Example 289) (200 mg, 0.35 mmol) in methanol/ethyl acetate (1:3) is added 20 mg Pd/C. The mixture is stirred under H2 atmosphere for 30 minutes. Filtration through a bed of celite and evaporation yields 178 mg of the title compound as a white solid. 1H NMR (CDCl3) δ 7.32-7.29 (m, 2H), 7.25-7.19 (m, 2H), 7.19-7.15 (m, 1H), 6.88-6.83 (m, 4H), 6.79-6.73 (m, 3H), 5.10 (dd, J=9.2, 5.6 Hz, 1H), 3.97-3.88 (m, 2H), 3.75-3.68 (m, 1H), 3.38 (dd, J=8.8, 6.0 Hz, 1H), 3.36 (t, J=6.4 Hz, 2H), 3.01 (s, 3H); HPLC-MS calculated for C24H23ClN2O5S (M+H+): 487.1, found 487.1.

Workup

  1. filtrationFiltration
  2. customthrough a bed of celite and evaporation

Sources & evidence

ORD record
ord-3166a8a5feca45209772ebb52f13d6e2
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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