Methanol → N-[5-(1-aminoethyl)-2-fluorophenyl]methanesulfonamide

HRID 75953Notes

Reaction equation

HRID 75953 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:10]\O)/[CH3:9])=[CH:4][C:3]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14].[H][H].CO>C1COCC1.[Ni].O>[NH2:10][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:4]=1)[CH3:9]

Participants

7

Reactant 3

HCID 887MethanolHCID 87395620HCID 87395620, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67426606N-[5-(1-aminoethyl)-2-fluorophenyl]methanesulfonamide

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-{2-Fluoro-5-[(1Z)—N-hydroxyethanimidoyl]phenyl}methanesulfonamide (Method 62, 200 mg, 812 μmol) was dissolved in 15 ml THF, to which was added Raney nickel 2800 slurry in water (200 μl). The mixture was charged with nitrogen and stirred over 1 atm of hydrogen. After 1 hour, MeOH (4 ml) was added and the reaction mixture was stirred overnight. The following morning the solution was filtered through celite, and the cake washed with MeOH, and the organic layer was concentrated to a yellow solid which was dried under high vacuum (181 mg, 96%). 1H NMR: 1.26 (d, 3H, CH3), 2.92 (s, 3H, SO2Me), 3.33 (HOD), 4.04 (q, 1H, CH), 5.70 (br, 2H, NH2), 7.06-7.16 (m, 2H, Ar), 7.35 (m, 1H, Ar). LC/MS: 0.79 min, 231.08 (M−H)−.

Workup

  1. additionThe mixture was charged with nitrogen
  2. filtrationThe following morning the solution was filtered through celite
  3. washthe cake washed with MeOH
  4. concentrationthe organic layer was concentrated to a yellow solid which
  5. customwas dried under high vacuum (181 mg, 96%)
  6. custom0.79 min, 231.08 (M−H)−

Sources & evidence

ORD record
ord-d9c208d1e8a440f9a7322e3619c7c740
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Reaction notes

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