Pyrazole → HCID 18538721, compound

HRID 2403434Notes

Reaction equation

HRID 2403434 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21]Br)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>CN(C)C=O>[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate

Product 1

HCID 18538721HCID 18538721, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of pyrazole (68 mgs) in anhydrous dimethylformamide was added sodium hydride (44 mgs). The reaction mixture was stirred at 50° C. for 25 minutes. 4-Bromomethyl-piperidine-1-carboxylic acid tert-butyl ester (280 mgs) in anhydrous dimethylformamide was added. The reaction mixture was stirred at 70° C. under argon for 2.5 hours. The reaction mixture was quenched with water (1 ml) and the solvents were removed in vacuo. The crude residue was partitioned between dichloromethane and water, dried (MgSO4) and the solvents removed in vacuo to give a crude product. This was purified using flash chromatography to yield 4-Pyrazol-1-ylmethyl-piperidine-1-carboxylic acid tert-butyl ester (148 mg).

Workup

  1. stirringThe reaction mixture was stirred at 70° C. under argon for 2.5 hours
  2. customThe reaction mixture was quenched with water (1 ml)
  3. customthe solvents were removed in vacuo
  4. customThe crude residue was partitioned between dichloromethane and water
  5. dry with materialdried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customto give a crude product
  8. customThis was purified

Sources & evidence

ORD record
ord-d03f03cfe435402f9420c61cd41ab6ad
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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