Sodium Azide → HCID 58790292, compound

HRID 418722Notes

Reaction equation

HRID 418722 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH3:41])=[O:32])=[CH:24][C:23]=3[F:43])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[N-:44]=[N+]=[N-].[Na+]>CN(C=O)C>[NH2:44][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:42])[CH2:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[O:40][CH3:41])=[O:32])=[CH:24][C:23]=3[F:43])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58790205HCID 58790205, compound

Product 1

HCID 58790292HCID 58790292, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 366 (0.19 g, 0.31 mmol) in DMF (5 mL) was added sodium azide (0.050 g, 0.77 mmol) and the reaction mixture was heated to 100° C. for 1 h. The mixture was then cooled, partitioned between ethyl acetate and water, the organic phase was collected, washed with water, brine, dried (anhydrous MgSO4), filtered, and concentrated. The residue was filtered through a short plug of silica, eluting with ethyl acetate, and the eluate was concentrated. The residue was dissolved in 1:1 ethyl acetate/methanol (30 mL) mixture; to this solution was added palladium (10% on carbon), and the suspension was stirred under an atmosphere of hydrogen for 3 h. It was then filtered through celite and concentrated. The residue was purified by flash chromatography (eluent 95:3:2 chloroform/methanol/NH4OH) to afford 367 (0.097 g, 52% yield): LRMS (M+H): 601.2.

Workup

  1. temperatureThe mixture was then cooled
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase was collected
  4. washwashed with water, brine
  5. dry with materialdried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. filtrationThe residue was filtered through a short plug of silica
  9. washeluting with ethyl acetate
  10. concentrationthe eluate was concentrated
  11. dissolutionThe residue was dissolved in 1:1 ethyl acetate/methanol (30 mL) mixture
  12. additionto this solution was added palladium (10% on carbon)
  13. filtrationIt was then filtered through celite
  14. concentrationconcentrated
  15. customThe residue was purified by flash chromatography (eluent 95:3:2 chloroform/methanol/NH4OH)

Sources & evidence

ORD record
ord-beef65ddc30e4050b207f73b333b00cd
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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