HCID 58275540, compound → 5-Aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamide

HRID 42362Notes

Reaction equation

HRID 42362 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][C:10]=1[F:17])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>Cl.CCO.[Pd]>[NH2:16][CH2:15][C:13]1[CH:12]=[CH:11][C:10]([F:17])=[C:9]([S:6]([NH:5][C:1]([CH3:3])([CH3:2])[CH3:4])(=[O:8])=[O:7])[CH:14]=1

Participants

4

Reactant 1

HCID 58275540HCID 58275540, compound

Product 1

HCID 287163695-Aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21887872Ethanol hydrochlorideSolvent

Procedure

A mixture of N-tert-butyl-5-cyano-2-fluoro-benzenesulfonamide (0.3 g) and Pd/C (50 mg) in 1N HCl/EtOH (1 ml 1N HCl in 10 ml EtOH) was stirred under H2 for 2 hours. The reaction mixture was filtered through a pad of diatomaceous earth, washed with MeOH and concentrated to about 3 ml. The residue was diluted with H2O and lyophilized to give 5-aminomethyl-N-tert-butyl-2-fluoro-benzenesulfonamide (0.27 g, 90% yield) as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of diatomaceous earth
  2. washwashed with MeOH
  3. concentrationconcentrated to about 3 ml
  4. additionThe residue was diluted with H2O

Sources & evidence

ORD record
ord-09448024350b4f38adf6624b4ecc03b1
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

Loading…