HCID 69083506, compound → HCID 69082589, compound

HRID 1023427Notes

Reaction equation

HRID 1023427 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=2)=[CH:3][CH:2]=1.[OH:20][CH:21]([C:33]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=1)[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]([NH2:32])=[O:31])[CH:24]=1>C(O)C.[Pd]>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=2)=[CH:5][CH:6]=1.[OH:20][CH:21]([C:33]1[CH:34]=[CH:35][C:36]([CH3:39])=[CH:37][CH:38]=1)[CH2:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30]([NH2:32])=[O:31])[CH:24]=1

Participants

6

Reactant 2

HCID 69083506HCID 69083506, compoundHCID 69085513HCID 69085513, compound

Product 2

HCID 69082589HCID 69082589, compoundHCID 69083506HCID 69083506, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To the solution of the mixture of [4-((E)-2-p-Tolyl-vinyl)-pyridin-2-yl]-urea and [4-(2-hydroxy-2-p-tolyl-ethyl)-pyridin-2-yl]-urea (36 mg) in ethanol (3 mL) is added 5% palladium on carbon (5 mg). The mixture is purged and back filled with hydrogen three times using a hydrogen balloon. Then the reaction is stirred for 3 hours under the hydrogen atmosphere. The palladium on carbon is filtered and the filtrate is purified by Gilson preparative HPLC to give 12 mg of [4-(2-p-tolyl-ethyl)-pyridin-2-yl]-urea and 3 mg of [4-(2-hydroxy-2-p-tolyl-ethyl)-pyridin-2-yl]-urea.

Workup

  1. customThe mixture is purged
  2. additionback filled with hydrogen three times
  3. filtrationThe palladium on carbon is filtered
  4. customthe filtrate is purified by Gilson preparative HPLC

Sources & evidence

ORD record
ord-eec5060305b54fc795251de1aa4422b1
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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