HCID 16753951, compound → HCID 16753952, compound

HRID 897373Notes

Reaction equation

HRID 897373 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[N+]=[N-].[H][H]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 16753951HCID 16753951, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 16753952HCID 16753952, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(azidomethyl)-5-fluoro-N,N-dimethylbenzenesulfonamide (3.57 g, 13.8 mmol) and 5% palladium on carbon (0.89 g, 25% w/w) in absolute ethanol (100 mL) was stirred under a balloon of hydrogen gas for one hour. The reaction was filtered through a small pack of celite and the filtrate was concentrated in vacuo to a yellow oil. The crude material was purified by preparative HPLC. (Gilson semi preparative HPLC system using a Waters Delta pak column (3(10×40 mm I.D.)cartridges, C18, 15 μm pore size) eluting with 5-95% acetonitrile/water (0.1% TFA) at 30 ml/min) to afford the desired product as a white solid.

Workup

  1. filtrationThe reaction was filtered through a small pack of celite
  2. concentrationthe filtrate was concentrated in vacuo to a yellow oil
  3. customThe crude material was purified by preparative HPLC
  4. washeluting with 5-95% acetonitrile/water (0.1% TFA) at 30 ml/min)

Sources & evidence

ORD record
ord-6cb1fd1acd84433785600c6ade26e6bb
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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