tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate → tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylate

HRID 1404595Notes

Reaction equation

HRID 1404595 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[N+:26]([O-:28])=[O:27]>CN(C=O)C>[CH3:15][N:16]([CH3:19])/[CH:17]=[CH:1]/[C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])[CH2:15][CH2:14]3)[CH:12]=2)=[CH:4][C:3]=1[N+:26]([O-:28])=[O:27]

Participants

3

Reactant 1

HCID 58532320tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 58532279tert-butyl 4-(4-{6-[(E)-2-(dimethylamino)ethenyl]-5-nitropyridin-3-yl}-1H-pyrazol-1-yl)piperidine-1-carboxylateYield 204.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (7.7 g) and N—N-dimethylformamide-dimethylacetal (DMF-DMA) (10g) in 50 ml of DMF was heated at 90° C. overnight and cooled to room temperature. The solvent was evaporated and the residue dissolved in DCM, which was washed with sat. NaHCO3 and brine, and evaporated to give a red solid, 9.0 g of crude product.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in DCM
  3. washwhich was washed with sat. NaHCO3 and brine
  4. customevaporated

Sources & evidence

ORD record
ord-aa59e4b182b644e19bb7698eeb4c1aa9
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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