Sodium Azide → HCID 21471655, compound

HRID 2294925Notes

Reaction equation

HRID 2294925 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[NH:24][C:23]4=[O:31])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[CH:5]=[N:4][CH:3]=1.[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C)C=O>[N:32]([C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:21][CH2:20][CH:19]([N:22]4[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[NH:24][C:23]4=[O:31])[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[CH:5]=[N:4][CH:3]=1)=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 21471590HCID 21471590, compound

Product 1

HCID 21471655HCID 21471655, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.15 g of 1,3-dihydro-1-{1-[1-(6-chloro-2-pyrazinecarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one, 0.26 g of sodium azide and 5 mL of anhydrous N,N-dimethylformamide was stirred for 24 h, then concentrated to dryness under reduced pressure. The residue was partitioned between 50 mL of chloroform and 5 mL of saturated sodium carbonate and the organic extracts dried over MgSO4. Removal of solvents under reduced pressure and drying under vacuum gave 0.16 g of crude 1,3-dihydro-1-{1-[1-(6-azido-2-pyrazinecarbonyl)piperidin-4-yl]piperidin-4-yl}-2H-benzimidazol-2-one.

Workup

  1. concentrationconcentrated to dryness under reduced pressure
  2. customThe residue was partitioned between 50 mL of chloroform and 5 mL of saturated sodium carbonate
  3. dry with materialthe organic extracts dried over MgSO4
  4. customRemoval of solvents under reduced pressure
  5. customdrying under vacuum

Sources & evidence

ORD record
ord-3e71674aad9e4fd493aea7797127f9f4
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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