N-[2-(3-benzyloxy-phenyl)-ethyl]-N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-5-trifluoromethyl-benzamide → N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-N-[2-(3-hydroxy-phenyl)-ethyl]-5-trifluoromethyl-benzamide

HRID 19810Notes

Reaction equation

HRID 19810 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][N:17]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([CH3:42])([CH3:41])[CH3:40])=[CH:35][CH:34]=2)[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([Cl:29])[C:20]=2[F:30])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:39]([C:36]1[CH:35]=[CH:34][C:33]([CH2:32][N:17]([CH2:16][CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=2)[C:18](=[O:31])[C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:26])[F:27])[CH:22]=[C:21]([Cl:29])[C:20]=2[F:30])=[CH:38][CH:37]=1)([CH3:42])([CH3:40])[CH3:41]

Participants

4

Reactant 1

HCID 68562844N-[2-(3-benzyloxy-phenyl)-ethyl]-N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-5-trifluoromethyl-benzamide

Product 1

HCID 68561896N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-N-[2-(3-hydroxy-phenyl)-ethyl]-5-trifluoromethyl-benzamideYield 80.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.1 g of N-[2-(3-benzyloxy-phenyl)-ethyl]-N-(4-tert-butyl-benzyl)-3-chloro-2-fluoro-5-trifluoromethyl-benzamide (1.84 mmol) in 50 ml ethyl acetate was hydrogenated over 0.33 g Pd/C-5%. After completion of the reaction the suspension was filtered off and concentrated in vacuo to give 0.75 g of a colorless amorphous material. MS: 508.4 [ISP (M+H)+].

Workup

  1. customAfter completion of the reaction the suspension
  2. filtrationwas filtered off
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0fc80271d9c146448b0abba18ce6e834
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

Loading…