Methanesulfonamide, N-[5-(1,1-dimethylethyl)-2-methoxy-3-nitrophenyl]- → N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

HRID 1423264Notes

Reaction equation

HRID 1423264 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:18]([O-])=O)[C:8]([O:16][CH3:17])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[NH2:18][C:7]1[C:8]([O:16][CH3:17])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:6]=1

Participants

4

Reactant 1

HCID 11231924Methanesulfonamide, N-[5-(1,1-dimethylethyl)-2-methoxy-3-nitrophenyl]-

Product 1

HCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 5 L hydrogenator was charged the product from step (viii) above (209.4 g, 0.693 mol), methanol (1675 mL, 8 volumes) and 10% Pd/C (10.2 g). The vessel was purged with 3×N2 and 3×H2 and then stirred under 0.3447 MPa (50 psi) H2 until no further exotherm was observed, with HPLC indicating 96.35% product and 1.10% starting material. The reaction was diluted with THF (314 mL) and the catalyst was removed via vacuum filtration (Cuno filter), before being washed with THF (1000 mL). The solvents were concentrated to isolate a light brown solid, which was dried under vacuum at 40° C. overnight. Yield=167.0 g (88.5%). HPLC purity 96.7%. Purity >95% by 1H NMR.

Workup

  1. customThe vessel was purged with 3×N2 and 3×H2
  2. additionThe reaction was diluted with THF (314 mL)
  3. customthe catalyst was removed via vacuum filtration (Cuno filter)
  4. washbefore being washed with THF (1000 mL)
  5. concentrationThe solvents were concentrated
  6. customto isolate a light brown solid, which
  7. customwas dried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-789d9c80a7a946eba29c2bdc98246e09
Source dataset
uspto-grants-2015_01
Patent number
US08927563B2

Reaction notes

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