Ethyl Acetate → (S)-4-Amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxypicolinamide

HRID 2370873Notes

Reaction equation

HRID 2370873 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:13]([C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=2)[NH:14][C:15](=[O:27])[C:16]2[CH:21]=[C:20]([N+:22]([O-])=O)[C:19]([O:25][CH3:26])=[CH:18][N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].CCOC(C)=O>[Ni].CO>[NH2:22][C:20]1[C:19]([O:25][CH3:26])=[CH:18][N:17]=[C:16]([C:15]([NH:14][C@@H:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:10])([F:11])[F:12])=[C:2]([F:1])[CH:3]=2)[C:28]2[C:33]([F:34])=[CH:32][CH:31]=[CH:30][N:29]=2)=[O:27])[CH:21]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 71144521(S)-N-((3-Fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxy-4-nitropicolinamide

Product 1

HCID 71144233(S)-4-Amino-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxypicolinamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a stirred suspension of Raney Nickel (0.4 g, Monarch, India) in MeOH (10 mL) was added (S)—N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-methoxy-4-nitropicolinamide (700 mg, 0.0014 mol) at rt. The reaction mixture was stirred under a hydrogen balloon for 2 h. After completion of the reaction, monitored by TLC (TLC eluent: 50% EtOAc in petroleum ether), the reaction mixture was filtered through Celite® brand filter agent and concentrated. The resulting product was triturated with petroleum ether to give the title compound as a white solid. MS (ESI, positive ion) m/z: 455.2 (M+H).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through Celite® brand
  3. filtrationfilter agent
  4. concentrationconcentrated
  5. customThe resulting product was triturated with petroleum ether

Sources & evidence

ORD record
ord-2bf4617e0ff543d1805156b3f32ab005
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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