HCID 86687995, compound → HCID 71144540, compound

HRID 2370855Notes

Reaction equation

HRID 2370855 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]([NH:10][C@@H:11]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)[C:12]2[C:17]([CH:18]=[CH2:19])=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:9])[CH:4]=[CH:3]1.[H][H]>[Pd].CCOC(C)=O>[CH2:18]([C:17]1[C:12]([C@H:11]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:22][CH:21]=2)[NH:10][C:8]([C:5]2[CH:4]=[CH:3][C:2](=[O:1])[NH:7][CH:6]=2)=[O:9])=[N:13][CH:14]=[CH:15][CH:16]=1)[CH3:19]

Participants

5

Reactant 2

HCID 86687995HCID 86687995, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71144540HCID 71144540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a 100 mL round bottom flask containing (S)-6-oxo-N-((4-(trifluoromethyl)phenyl)(3-vinylpyridin-2-yl)methyl)-1,6-dihydropyridine-3-carboxamide (40 mg, 0.100 mmol, Example 363) was added EtOAc (20 mL). The resulting mixture was then stirred at 23° C. for 2 min. At this time, Pd/C (10%, 20 mg) was added before a balloon of hydrogen was bubbled through the mixture. The reaction was stirred for 2 h under hydrogen (1 atm) and was then filtered though a plug of Celite® brand filter agent and eluted with EtOAc (50 mL). The solvent was removed, and the material was placed on high vacuum for 1 h to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.67 (d, J=6.9 Hz, 1H), 8.53 (d, J=4.7 Hz, 1H), 8.07 (d, J=2.2 Hz, 1H), 7.94 (dd, J=9.6, 2.4 Hz, 1H), 7.36-7.67 (m, 5H), 7.27-7.36 (m, 1H), 6.60 (d, J=9.5 Hz, 1H), 6.50 (d, J=6.7 Hz, 1H), 2.63-2.82 (m, 1H), 2.36-2.62 (m, 1H), 1.11 (t, J=7.5 Hz, 3H). MS (ESI, positive ion) m/z: 402.1 (M+H).

Workup

  1. customwas bubbled through the mixture
  2. stirringThe reaction was stirred for 2 h under hydrogen (1 atm)
  3. filtrationwas then filtered though a plug of Celite® brand
  4. filtrationfilter agent
  5. washeluted with EtOAc (50 mL)
  6. customThe solvent was removed
  7. waitthe material was placed on high vacuum for 1 h

Sources & evidence

ORD record
ord-f797d782aa03466d9e4f0537b73da151
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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