HCID 22615760, compound → HCID 22615711, compound

HRID 366501Notes

Reaction equation

HRID 366501 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[N:19]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C.O1CCCC1>[C:26]([C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[N:19]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:18]=[C:17]2[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)#[N:27]

Participants

4

Reactant 1

HCID 22615760HCID 22615760, compound

Product 1

HCID 22615711HCID 22615711, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

10% Palladium on carbon (0.49 g) was added to a solution of 1-benzyloxycarbonyl-4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine (0.98 g, 2.24 mmol) [prepared as described in Step 2 above] in 80% ethanol/tetrahydrofuran (10 ml) under an argon atmosphere. The reaction mixture was stirred under an atmosphere of hydrogen gas (1 atm) for 2 h. The reaction mixture was degassed, filtered through Celite and concentrated in vacuo to give 4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine (97%) as a white solid. This material was converted to N-hydroxy-1-[4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine-1-sulfonyl]-piperidine-2-(R)-carboxamnide by converting it to 4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine-1-sulfonyl chloride by following Example 16, Step 1, coupling the sulfonyl chloride with (R)-pipecolinic acid (L)-tartrate salt to give 1-[4-(5-cyano-1-methanesulfonyl-indol-3-yl)piperidine-1-sulfonyl]piperidine-2-(R)-carboxylic acid (86%) by following Example 14, Step 6 and then converting the acid to the final compound by following Example 16, Steps 3 and 5; mp: 143.3-143.9° C.

Workup

  1. customThe reaction mixture was degassed
  2. filtrationfiltered through Celite
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be65f907724f4576b9ac50c4d8003c08
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

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