HCID 18727129, compound → HCID 18727137, compound

HRID 843032Notes

Reaction equation

HRID 843032 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([N:14]2[CH2:19][CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])[C@@H:7]([C:27]([OH:29])=[O:28])[CH2:6]1)=[O:4]>O1CCCC1.C(O)C.[Pd]>[CH3:1][N:2]([CH3:30])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)[CH2:16][CH2:15]2)(=[O:13])=[O:12])[C@@H:7]([C:27]([OH:29])=[O:28])[CH2:6]1)=[O:4]

Participants

4

Reactant 1

HCID 18727129HCID 18727129, compound

Product 1

HCID 18727137HCID 18727137, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 4-(N,N-dimethylaminocarbonyl)-1-[4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine-1-sulfonyl]piperazine-2-(R)-carboxylic acid (1.39 g, 3.16 mmol) [prepared as described in Example 28, Steps 1-4] and 10% Pd/C (0.7g) in 10 % tetrahydrofuran/ethanol (45 ml) was stirred under an atmosphere of hydrogen (1 atm) overnight. The reaction mixture was filtered through Celite with excess ethanol and the filtrate was concentrated in vacuo to give 4-(N,N-dimethylaminocarbonyl)-1-[4-(4-fluorophenyl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxylic acid (88%) as a white solid. This material was converted to N-hydroxy-4-dimethylaminocarbonyl-1-[4-(4-fluorophenyl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide by following the procedure described in Example 28, Step 5 above.

Workup

  1. filtrationThe reaction mixture was filtered through Celite with excess ethanol
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6af6ea07a14f4428a80e5f362c8e87ef
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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