Sodium Azide → HCID 86662089, compound

HRID 1959470Notes

Reaction equation

HRID 1959470 reaction equation
C(OC([N:8]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:9]1[N:10]=[CH:11][C:12]([C:36]2[CH2:41][CH2:40][CH:39](CS([O-])(=O)=O)[CH2:38][CH:37]=2)=[N:13][C:14]=1[C:15]1[O:16][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:18][N:19]=1)=O)(C)(C)C.[N-:54]=[N+:55]=[N-:56].[Na+]>CN(C=O)C>[N:54]([CH:39]1[CH2:40][CH2:41][C:36]([C:12]2[N:13]=[C:14]([C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH3:28])[C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[CH:22][CH:21]=4)=[N:18][N:19]=3)[C:9]([NH:8][C:47]([O:49][C:50]([CH3:52])([CH3:51])[CH3:53])=[O:48])=[N:10][CH:11]=2)=[CH:37][CH2:38]1)=[N+:55]=[N-:56]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86662090HCID 86662090, compound

Product 1

HCID 86662089HCID 86662089, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of [4-[5-[bis(tert-butoxycarbonyl)amino]-6-[5-[4-[[tert-butoxycarbonyl(methyl)amino]methyl]phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]cyclohex-3-en-1-yl]methanesulfonate (138 mg, 0.18 mmol) in anhydrous DMF (1 mL) was added sodium azide (59 mg, 0.91 mmol) and the reaction mixture was heated at 70° C. under an atmosphere of nitrogen for 15 h. The reaction mixture was cooled to room temperature, quenched with water and diluted with EtOAc. An aqueous saturated brine solution was added, the layers were separated and the organic layer was washed twice more with an aqueous saturated brine solution. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure to a brown oil to provide tert-butyl N-[[4-[5-[6-(4-azidocyclohexen-1-yl)-3-(tert-butoxycarbonylamino)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (103 mg, 94%), which was used without any further purification in the next step. LC/MS m/z 604.7 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water
  3. additiondiluted with EtOAc
  4. additionAn aqueous saturated brine solution was added
  5. customthe layers were separated
  6. washthe organic layer was washed twice more with an aqueous saturated brine solution
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure to a brown oil

Sources & evidence

ORD record
ord-0309d7041fcf4b8084f4d325eef5f101
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…