Dimethylamine → 2,2-Dimethylpropyl 4-{4-[5-(dimethylamino)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

HRID 421828Notes

Reaction equation

HRID 421828 reaction equation
ClC(Cl)(Cl)[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:21])[CH2:16][CH2:15]3)[CH:9]=2)[N:4]=1.[CH3:30][NH:31][CH3:32]>C(O)C>[CH3:30][N:31]([CH3:32])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([N:14]3[CH2:15][CH2:16][N:17]([C:20]([O:22][CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:21])[CH2:18][CH2:19]3)[CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 119927082,2-Dimethylpropyl 4-{4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

Product 1

HCID 119928042,2-Dimethylpropyl 4-{4-[5-(dimethylamino)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,2-Dimethylpropyl 4-{4-[5-(trichloromethyl)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate (133 mg) obtained in Example 32 was dissolved in ethanol (4 mL), and aqueous 50% dimethylamine solution (1 mL) was added thereto, and stirred at room temperature for 3 hours. Then, the solvent was evaporated away and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 49.1 mg of the entitled compound as a colorless oil.

Workup

  1. customThen, the solvent was evaporated away
  2. customthe resulting residue was isolated
  3. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2e302ca676864f0fa19b61936a7e2d2d
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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