Sodium Azide → HCID 178421868, compound

HRID 1405319Notes

Reaction equation

HRID 1405319 reaction equation
[CH3:1][N:2]([CH:25]([CH3:27])[CH3:26])[C:3]1[C:4]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19]([CH3:24])=[CH:18]3)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][C:9]([C:13]#[N:14])=[CH:8][CH:7]=2.[N-:28]=[N+:29]=[N-:30].[Na+]>CS(C)=O.O.[Zn+2].[Br-].[Br-]>[CH:25]([N:2]([CH3:1])[C:3]1[C:4]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][C:19]([CH3:24])=[CH:18]3)=[N:5][C:6]2[C:11](=[CH:10][C:9]([C:13]3[NH:30][N:29]=[N:28][N:14]=3)=[CH:8][CH:7]=2)[N:12]=1)([CH3:27])[CH3:26]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 70654432HCID 70654432, compound

Product 1

HCID 178421868HCID 178421868, compoundYield 21.2%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 3-[methyl(propan-2-yl)amino]-2-(2-methyl-1H-indol-5-yl)quinoxaline-6-carbonitrile (200 mg, 0.56 mmol) in DMSO (20 ml) was added NaN3 (110 mg, 1.69 mmol) in water (2 ml), and ZnBr2 (64 mg, 0.28 mmol). The resulting solution was stirred overnight at 130° C. and then quenched with water (200 ml). The pH was adjusted to 3 with HCl (2N). Then the solution was extracted with ethyl acetate (4×50 ml) and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (10%-15% dichloromethane in methanol) to afford N-isopropyl-N-methyl-3-(2-methyl-1H-indol-5-yl)-7-(1H-tetrazol-5-yl)quinoxalin-2-amine as an orange solid (47.4 mg, 21%).

Workup

  1. customquenched with water (200 ml)
  2. extractionThen the solution was extracted with ethyl acetate (4×50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a residue, which
  6. customwas purified by silica gel column chromatography (10%-15% dichloromethane in methanol)

Sources & evidence

ORD record
ord-f199fe4c340c444284990f9530034d38
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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