Ethyl Acetate → HCID 178508027, compound

HRID 509441Notes

Reaction equation

HRID 509441 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:13]([C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[NH:14][C:15](=[O:26])[C:16]2[CH:21]=[C:20]([OH:22])[C:19]([N+:23]([O-])=O)=[CH:18][N:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]([F:12])([F:11])[F:10].O.NN.CCOC(C)=O>CO.CCCCCC.[Ni]>[NH2:23][C:19]1[C:20]([OH:22])=[CH:21][C:16]([C:15]([NH:14][C@@H:13]([C:4]2[CH:5]=[CH:6][C:7]([O:8][C:9]([F:11])([F:10])[F:12])=[C:2]([F:1])[CH:3]=2)[C:27]2[C:32]([F:33])=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])=[N:17][CH:18]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 178523849HCID 178523849, compound

Product 1

HCID 178508027HCID 178508027, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a stirred solution of (S)—N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-4-hydroxy-5-nitropicolinamide (0.35 g, 0.0007 mol) in MeOH (10 mL) was added Raney Ni (0.3 g, Monarch), followed by hydrazine hydrate (2 mL, Aldrich) added in a drop-wise fashion at rt. The reaction mixture was stirred for 3 h. After completion of the reaction (monitored by TLC, 50% EtOAc in hexane), the reaction mixture was filtered through Celite® brand filter agent and concentrated providing a residue. The residue was triturated with Et2O, filtered dried under vacuum to give the title compound as a brown solid. 1H NMR (DMSO-d6) δ: 9.41 (d, J=7.5 Hz, 1H), 8.55 (d, J=4.2 Hz, 1H), 7.83-7.78 (m, 2H), 7.54-7.44 (m, 3H), 7.27 (d, J=9.9 Hz, 2H), 6.46 (d, J=6.9 Hz, 1H), 5.29 (s, 2H).

Workup

  1. additionadded in a drop-wise fashion at rt
  2. filtrationthe reaction mixture was filtered through Celite® brand
  3. filtrationfilter agent
  4. concentrationconcentrated
  5. customproviding a residue
  6. customThe residue was triturated with Et2O
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3b7c2a3d0d324a7a982075e1adc3518d
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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