Sodium hydride → tert-Butyl 4-{3-ethyl-1-[4-(methylthio)benzyl]-1H-pyrazol-4-yl}-piperidine-1-carboxylate

HRID 1635965Notes

Reaction equation

HRID 1635965 reaction equation
[CH2:1]([C:3]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[CH:6][NH:5][N:4]=1)[CH3:2].[H-].[Na+].[CH2:23]([S:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Cl)=[CH:28][CH:27]=1)C>CN(C=O)C>[CH2:1]([C:3]1[C:7]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:5]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([S:25][CH3:23])=[CH:27][CH:28]=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 186738584-(Ethylthio)benzyl chloride2×HCID 178438034HCID 178438034, compound

Product 1

HCID 18673862tert-Butyl 4-{3-ethyl-1-[4-(methylthio)benzyl]-1H-pyrazol-4-yl}-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-ethyl-4-(N-t-butoxycarbonylpiperid-4-yl)-1H-pyrazole (0.83 g, 2.97 mmol, from Step B) in 4 mL DMF was cooled to 0° C. and sodium hydride (155 mg, 3.87 mmol, 60% dispersion in mineral oil) was added cautiously. The mixture was warmed to rt and 4-(ethylthio)benzyl chloride (crude material from Step C) in 6 mL DMF was added. The mixture was stirred for 14 h. The mixture was concentrated and the residue was taken up in methylene chloride. The solution was washed with water and sat'd sodium chloride then dried over magnesium sulfate and concentrated. Flash chromatography (40 g silica, 4/1 hexane/EtOAc) afforded the product.

Workup

  1. concentrationThe mixture was concentrated
  2. washThe solution was washed with water
  3. dry with materialthen dried over magnesium sulfate
  4. concentrationconcentrated
  5. customFlash chromatography (40 g silica, 4/1 hexane/EtOAc) afforded the product

Sources & evidence

ORD record
ord-dd75f167be734a48aa882ad8f107fe33
Source dataset
uspto-grants-2003_01
Patent number
US06511994B2

Reaction notes

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