HCID 25018894, compound → HCID 25018895, compound

HRID 1878714Notes

Reaction equation

HRID 1878714 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]1[C:7]1[CH:8]=[CH:9][C:10](=[O:28])[N:11]([CH2:13][CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:26][CH3:27])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:12]=1>[Pt]=O.C1COCC1>[CH3:27][O:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([O:15][CH2:14][CH2:13][N:11]3[CH:12]=[C:7]([CH:2]4[CH2:3][CH2:4][CH2:5][CH2:6][O:1]4)[CH:8]=[CH:9][C:10]3=[O:28])=[CH:17][CH:18]=[N:19]2)=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 25018894HCID 25018894, compound

Product 1

HCID 25018895HCID 25018895, compound

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 15 mL, 1-neck round bottom flask was charged with 5-(5,6-dihydro-2H-pyran-2-yl)-1-(2-(7-methoxyquinolin-4-yloxy)ethyl)pyridin-2(1H)-one (0.006 g, 0.02 mmol), 2 mL dry THF, and a stirbar. The solution was cooled to 0° C., and carefully evacuated and refilled with N2 (three times). To the stirring solution was added Platinum oxide (0.004 g, 0.02 mmol). The solution was carefully evacuated and refilled with hydrogen from a balloon. The cooling bath was removed, and the reaction was stirred overnight. The solution was filtered through a 0.22 uM frit, and the filtrate was concentrated in vacuo. The residue was dissolved in 1 mL EtOH and treated with Silica propyl sulfonic acid (Silicycle, Inc., 0.04 g, 0.03 mmol). The slurry was swirled occasionally for 15 min, filtered and washed with EtOH (2×2 mL). The silica was then eluted with 1 mL of 2N NH3 in EtOH, followed by 2 mL of EtOH. The ammonia solution was concentrated in vacuo to afford 1-(2-(7-methoxyquinolin-4-yloxy)ethyl)-5-(tetrahydro-2H-pyran-2-yl)pyridin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 1.36-1.49 (m, 1H) 1.55-1.70 (m, 3H) 1.70-1.78 (m, 1H) 1.89-1.97 (m, 1H) 3.54-3.64 (m, 1H) 3.94 (s, 3H) 4.07-4.18 (m, 2H) 4.43-4.54 (m, 4H) 6.56 (d, J=9.29 Hz, 1H) 6.62 (d, J=5.28 Hz, 1H) 7.11 (dd, J=9.19, 2.54 Hz, 1H) 7.30 (dd, J=9.34, 2.49 Hz, 1H) 7.36 (d, J=2.54 Hz, 1H) 7.55 (d, J=2.54 Hz, 1H) 8.05 (d, J=9.10 Hz, 1H) 8.64 (d, J=5.28 Hz, 1H). 13C NMR (101 MHz, CDCl3) δ ppm 23.59 (s, 1 C) 25.71 (s, 1 C) 33.10 (s, 1 C) 49.18 (s, 1 C) 55.47 (s, 1 C) 65.75 (s, 1 C) 69.01 (s, 1 C) 76.55 (s, 1 C) 99.42 (s, 1 C) 107.11 (s, 1 C) 115.71 (s, 1 C) 118.42 (s, 1 C) 120.46 (s, 1 C) 121.23 (s, 1 C) 122.95 (s, 1 C) 135.65 (s, 1 C) 138.91 (s, 1 C) 151.13 (s, 1 C) 151.70 (s, 1 C) 160.84 (s, 1 C) 160.98 (s, 1 C) 162.22 (s, 1 C). MS (ESI pos. ion) m/z (MH+): 381.2, calcd for C22H24N2O4+H+=381.2.

Workup

  1. customcarefully evacuated
  2. additionrefilled with N2 (three times)
  3. customThe solution was carefully evacuated
  4. additionrefilled with hydrogen from a balloon
  5. customThe cooling bath was removed
  6. filtrationThe solution was filtered through a 0.22 uM frit
  7. concentrationthe filtrate was concentrated in vacuo
  8. dissolutionThe residue was dissolved in 1 mL EtOH
  9. additiontreated with Silica propyl sulfonic acid (Silicycle, Inc., 0.04 g, 0.03 mmol)
  10. waitThe slurry was swirled occasionally for 15 min
  11. filtrationfiltered
  12. washwashed with EtOH (2×2 mL)
  13. washThe silica was then eluted with 1 mL of 2N NH3 in EtOH
  14. concentrationThe ammonia solution was concentrated in vacuo

Sources & evidence

ORD record
ord-f463227cc8fd481ea5b729ce641cca0e
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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