HCID 68069072, compound → HCID 67284579, compound

HRID 1184441Notes

Reaction equation

HRID 1184441 reaction equation
[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[CH:9][C:10](/[CH:12]=[CH:13]/[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][C:5]=2[NH:4][C:3]1=[O:19]>[Pd].CCO>[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:11][C:5]=2[NH:4][C:3]1=[O:19]

Participants

4

Reactant 1

HCID 68069072HCID 68069072, compound

Product 1

HCID 67284579HCID 67284579, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 100 mL round bottom flask equipped with a magnetic stir bar was added 183 (67 mg, 0.256 mmol), Pd/C (10% by weight, 5 mg) and EtOH (2 mL). The mixture was stirred under a hydrogen atmosphere (balloon) for 18 h. The reaction was filtered and concentrated in vacuo to give the title compound as a white solid (62 mg, 92% yield): 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (t, J=7.07 Hz, 3H) 1.39 (d, J=6.82 Hz, 3H) 2.54 (t, J=7.33 Hz, 2H) 2.75 (t, J=7.45 Hz, 2H) 4.04 (q, J=7.24 Hz, 2H) 4.56-4.63 (m, 1H) 6.71 (d, J=1.77 Hz, 1H) 6.76 (dd, J=8.08, 2.02 Hz, 1H) 6.85 (d, J=8.34 Hz, 1H) 10.61 (s, 1H). ESI-MS: m/z 264.2 (M+H)+.

Workup

  1. customIn a 100 mL round bottom flask equipped with a magnetic stir bar
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3e40bb62f8f4e06bd67852b88309531
Source dataset
uspto-grants-2014_03
Patent number
US08669249B2

Reaction notes

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