HCID 59548815, compound → HCID 59548769, compound

HRID 1810977Notes

Reaction equation

HRID 1810977 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[C:5]([NH:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[C:15]1[CH2:16][CH2:17][N:18]([C:21](=[O:30])[CH2:22][N:23]2[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24]2)[CH2:19][CH:20]=1)=[O:6]>C(O)C.[Pd]>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([CH:15]2[CH2:16][CH2:17][N:18]([C:21](=[O:30])[CH2:22][N:23]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24]3)[CH2:19][CH2:20]2)=[C:8]([NH:7][C:5](=[O:6])[C:4]2[CH:31]=[CH:32][CH:33]=[CH:2][CH:3]=2)[CH:13]=1

Participants

4

Reactant 1

HCID 59548815HCID 59548815, compound

Product 1

HCID 59548769HCID 59548769, compoundYield 10.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-chloro-N-(5-chloro-2-{1-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-phenyl)-benzamide (0.100 g, 0.207 mmol) in ethanol (5 mL) is added Pd on 5% activated carbon (10 mg) in a round bottom flask and the mixture is purged three times and back filled with H2 using a H2 filled balloon. The reaction is allowed to stir at room temperature for 20 h. The reaction is filtered through a pad of diatomaceous earth and washed with MeOH. The filtrate is concentrated and purified via preparative HPLC. Removal of the solvent gives 0.010 g of N-(5-chloro-2-{1-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-phenyl)-benzamide in 10% yield. MS MH+=450.2 and 0.030 g of N-(2-{1-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-phenyl)-benzamide in 35% yield. MS MH+=417.3.

Workup

  1. customthe mixture is purged three times
  2. additionback filled with H2 using a H2 filled balloon
  3. filtrationThe reaction is filtered through a pad of diatomaceous earth
  4. washwashed with MeOH
  5. concentrationThe filtrate is concentrated
  6. custompurified via preparative HPLC
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-67f7ccf11f124c8e91dca00492df38d8
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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