HCID 178515673, compound → HCID 178515670, compound

HRID 1161771Notes

Reaction equation

HRID 1161771 reaction equation
C([O:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][N:16]([CH:19]3[CH2:27][CH2:26][C:22]4[NH:23][CH:24]=[N:25][C:21]=4[CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.CO.[OH-].[Pd+2].[OH-]>[Cl:31][C:29]1[CH:30]=[C:9]([OH:8])[CH:10]=[C:11]([Cl:32])[C:12]=1[CH2:13][CH:14]1[CH2:18][CH2:17][N:16]([CH:19]2[CH2:27][CH2:26][C:22]3[NH:23][CH:24]=[N:25][C:21]=3[CH2:20]2)[C:15]1=[O:28]

Participants

5

Reactant 1

HCID 178515673HCID 178515673, compound

Product 1

HCID 178515670HCID 178515670, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add palladium hydroxide to a nitrogen purged solution of 3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-1H-benzoimidazol-5-yl)-pyrrolidin-2-one (4.3 g, 9.2 mmol) (Preparation 12) in 50 ml of ethyl acetate and 15 ml of methanol. Add about 22 psi of pressurized nitrogen and stir for 16 h. Filter this mixture and concentrate to afford 3-(2,6-Dichloro-4-hydroxy-benzyl)-1-(4,5,6,7-tetrahydro-1H-benzoimidazol-5-yl)-pyrrolidin-2-one as solid product (2 g). MS: m/z (M+1)=380.

Workup

  1. additionAdd about 22 psi of pressurized nitrogen
  2. filtrationFilter this mixture
  3. concentrationconcentrate

Sources & evidence

ORD record
ord-f1ee0d3d7ab14274be5b415fdccebe2c
Source dataset
uspto-grants-2010_10
Patent number
US07820659B2

Reaction notes

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