Sodium Azide → HCID 86630625, compound

HRID 643713Notes

Reaction equation

HRID 643713 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH2:10][C:11]([S:14]([C:17]1[CH:34]=[CH:33][C:20]2[N:21]([CH2:29][CH:30]3[CH2:32][CH2:31]3)[C:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[N:23][C:19]=2[CH:18]=1)(=[O:16])=[O:15])([CH3:13])[CH3:12])(=O)=O>CN(C=O)C>[N:1]([CH2:13][C:11]([S:14]([C:17]1[CH:34]=[CH:33][C:20]2[N:21]([CH2:29][CH:30]3[CH2:31][CH2:32]3)[C:22]([CH2:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[N:23][C:19]=2[CH:18]=1)(=[O:16])=[O:15])([CH3:10])[CH3:12])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86630624HCID 86630624, compound

Product 1

HCID 86630625HCID 86630625, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
160 °C

Procedure

To a solution of sodium azide (176 mg, 2.70 mmol) in N,N′-dimethylformamide (5 mL) was added 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropyl methanesulfonate (Step I, 411 mg, 0.90 mmol) in N,N′-dimethylformamide (3 mL) at room temperature. The mixture was stirred at 160° C. for 24 h. The mixture was washed with ethyl acetate (20 mL×3) and water (30 mL). The combined organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:2 as eluent) to afford the title compound (265 mg) as a white amorphous.

Workup

  1. washThe mixture was washed with ethyl acetate (20 mL×3) and water (30 mL)
  2. dry with materialThe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=5:2 as eluent)

Sources & evidence

ORD record
ord-5ad3b316735f4d11ba65e528637d5276
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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