HCID 22046313, compound → HCID 22046461, compound

HRID 1821732Notes

Reaction equation

HRID 1821732 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[NH:12][C:13]([NH:15][C:16]1[CH:21]=[N:20][CH:19]=[CH:18][N:17]=1)=[O:14]>CN(C=O)C.[Pd]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([NH:12][C:13]([NH:15][C:16]2[CH:21]=[N:20][CH:19]=[CH:18][N:17]=2)=[O:14])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 22046313HCID 22046313, compound2×

Product 1

HCID 22046461HCID 22046461, compoundYield 41.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of (2-methoxy-4-nitrophenyl)-3-pyrazin-2-yl-urea (Compound 65, Example 9) (7.9 g, 27 mmol) in DMF (300 mL) was shaken under H2in the presence of Pd/C catalyst (1.6 g, 10% Pd) at 110° C. for 4 h. The mixture was filtered through a pad of celite using an additional 200 mL of DMF. The filtrate was concentrated in vacuo and the residue was recrystallized from ethanol (with a hot filtration step) to yield the light gray product (2.9 g, 41%). 1H NMR (300 MHz, d6-DMSO) δ: 9.83 (s, 1H), 9.50 (s, 1H), 8.86 (s, 1H), 8.28 (s, 1H), 8.19 (d, J=2.5 Hz, 1H), 7.64 (d, J=8.5 Hz, 1H), 6.31 (d, J=2.0 Hz, 1H), 6.13 (dd, J=8.5, 2.0 Hz, 1H), 4.92 (s, 2H), 3.79 (s, 3H). 13C NMR (75 Mhz, d6-DMSO) δ: 151.6, 150.0, 149.6, 145.2, 140.9, 136.9, 135.1, 121.6, 116.8, 105.5, 98.0, 55.4.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was recrystallized from ethanol (
  4. filtrationwith a hot filtration step)

Sources & evidence

ORD record
ord-8e39d185f67741859d2f34831865b0e7
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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