HCID 86760621, compound → HCID 24770888, compound

HRID 2116626Notes

Reaction equation

HRID 2116626 reaction equation
[N:1]([C@@H:4]([CH3:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([NH2:17])=[O:16])[CH:13]=2)[CH:8]=[N:7]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C@@H:4]([CH3:18])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([NH2:17])=[O:16])[CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 1

HCID 86760621HCID 86760621, compound

Product 1

HCID 24770888HCID 24770888, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Step B (0.14 g, 0.55 mmol) in ethanol (10 mL) was added Pd/C (10%, 0.01 g) under a nitrogen atmosphere at room temperature. The resultant suspension was stirred for 18 h under a hydrogen atmosphere. The reaction was filtered through a filter aide and the filtrate was concentrated in vacuo to give a solid (0.09 g, 75%): mp 170-172° C.; MS (ES) m/z 219 (M+); 1H NMR (DMSO-d6) 8.25 (1H, s), 8.12 (1H, s), 8.04 (1H, br s), 7.80 (1H, d, J=8.0 Hz), 7.63 (1H, d, J=8.0 Hz), 7.44 (1H, s), 4.27 (2H, m), 3.34 (1H, m), 0.96 (3H, d, J=6.0 Hz). Analysis. Calculated for C11H14N4O: C, 60.53; H, 6.47; N, 25.67. Found: C, 60.37; H, 6.33; N, 25.48.

Workup

  1. filtrationThe reaction was filtered through a filter aide
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f87943b0f25946b0964b0fa9238263c9
Source dataset
uspto-grants-2008_10
Patent number
US07439262B1

Reaction notes

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