Sodium Azide → HCID 178452278, compound

HRID 1157337Notes

Reaction equation

HRID 1157337 reaction equation
C([C:3]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[CH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)#N.[N-:24]=[N+:25]=[N-:26].[Na+]>CS(C)=O>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]1[NH:26][N:25]=[N:24][C:3]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 68694406HCID 68694406, compound

Product 1

HCID 178452278HCID 178452278, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of tert-butyl 4-(1-cyano-2-(pyridin-2-yl)vinyl)piperazine-1-carboxylate (2.5 g), sodium azide (0.4 g) were taken in dry DMSO (4 ml) and heated to 110° C. overnight. The reaction mixture was carefully quenched with water (10 ml) and the reaction mixture was extracted with dichloromethane (3×10 ml). The combined organic layer was washed with brine (10 ml), dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using methanol:chloroform (1:9) as an eluent to afford tert-butyl 4-(5-(pyridin-2-yl)-1H-1,2,3-triazol-4-yl)piperazine-1-carboxylate as white solid.

Workup

  1. customThe reaction mixture was carefully quenched with water (10 ml)
  2. extractionthe reaction mixture was extracted with dichloromethane (3×10 ml)
  3. washThe combined organic layer was washed with brine (10 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-851bff7de383419fa29e94186a7394a6
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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