Ethyl Acetate → N-(3-Aminopyridin-2-yl)-N-methylmethanesulfonamide

HRID 472373Notes

Reaction equation

HRID 472373 reaction equation
[CH3:1][N:2]([C:7]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][N:8]=1)[S:3]([CH3:6])(=[O:5])=[O:4].[H][H].C(OCC)(=O)C>[Pd].CO>[NH2:13][C:12]1[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 67478941N-Methyl-N-(3-nitropyridin-2-yl)methanesulfonamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57416061N-(3-Aminopyridin-2-yl)-N-methylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(3-Amino-pyridin-2-yl)-N-methyl-methanesulfonamide was prepared from N-methyl-N-(3-nitro-pyridin-2-yl)-methanesulfonamide (6.20 g, 26.8 mmol)(prepared as described in J. Med. Chem., 2007, 50, 3431) via hydrogenation using a Paar apparatus with 10% Palladium on Carbon (50% Wet) (5:45:50, Palladium:carbon black:Water, 5.71 g, 2.68 mmol) and Hydrogen (50 psi) in 2:1 ethyl acetate:methanol (150 mL). The mixture was shaken on a Paar apparatus until adsorption of hydrogen ceased. The mixture was degassed, backflushed with nitrogen, filtered through a plug of diatomaceous earth and rinsed with dichloromethane. The filtrate was evaporated under reduced pressure. Product isolated as brown solid (5.15 g, 95%). 1H NMR (400 MHz, CDCl3, δ, ppm): 7.85 (dd, J=3.7, 2.5 Hz, 1H), 7.10-7.08 (m, 2H), 4.24 (br s, 2H), 3.23 (s, 3H), 3.08 (s, 3H). MS=202 (MH)+.

Workup

  1. customThe mixture was degassed
  2. filtrationfiltered through a plug of diatomaceous earth
  3. washrinsed with dichloromethane
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-95c7fa40bba64d1bb194d0cf92e25a99
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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