Ethyl Acetate → HCID 178507640, compound

HRID 2370840Notes

Reaction equation

HRID 2370840 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]([NH:17][C@@H:18]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[C:28]([F:37])[CH:27]=2)[C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:16])[CH:12]=[CH:11][C:10]=1[N+:38]([O-])=O)C1C=CC=CC=1.[H][H].CCOC(C)=O>C1COCC1.[Pd]>[NH2:38][C:10]1[CH:11]=[CH:12][C:13]([C:15]([NH:17][C@@H:18]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[C:28]([F:37])[CH:27]=2)[C:19]2[C:24]([F:25])=[CH:23][CH:22]=[CH:21][N:20]=2)=[O:16])=[N:14][C:9]=1[OH:8]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 71144022(S)-6-(Benzyloxy)-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-nitropicolinamideHCID 178418361HCID 178418361, compound

Product 1

HCID 178507640HCID 178507640, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of (S)-6-(benzyloxy)-N-((3-fluoro-4-(trifluoromethoxy)phenyl)(3-fluoropyridin-2-yl)methyl)-5-nitropicolinamide (800 mg, 0.0014 mol) in THF (8 mL), was added 10% Pd/C (800 mg, Aldrich). The reaction mixture was stirred under hydrogen atmosphere in the form of hydrogen bladder (˜20-22 PSI) for 12 h at room temperature. After completion of the reaction (monitored by TLC, 100% EtOAc), the reaction mixture was filtered through Celite® brand filter agent, the filtrate dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 11.00 (s, 1H), 9.13 (d, J=6 Hz, 1H), 8.46 (d, J=4 Hz, 1H), 7.79 (t, J=9.2 Hz, 1H), 7.57-7.46 (m, 3H), 7.33 (d, J=8.4 Hz, 1H), 7.08 (br. s., 1H), 6.62 (d, J=7.6 Hz, 1H), 6.40 (br. s., 1H), 5.83 (br. s., 2H). MS (ESI, positive ion) m/z: 440.9 (M+H).

Workup

  1. filtrationthe reaction mixture was filtered through Celite® brand
  2. filtrationfilter agent
  3. dry with materialthe filtrate dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ad7a52f7f78d47589628fc916e0ea59c
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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