HCID 86760620, compound → HCID 24770889, compound

HRID 2116624Notes

Reaction equation

HRID 2116624 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[CH2:15][CH:16]([N:18]=[N+]=[N-])[CH3:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[N:11][N:12]2[CH2:15][C@@H:16]([NH2:18])[CH3:17])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86760620HCID 86760620, compound

Product 1

HCID 24770889HCID 24770889, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the product from Step C (0.20 g, 0.73 mmol) in ethanol (10 mL) was added Pd/C (10%, 0.01 g) under nitrogen atmosphere at room temperature. The resultant suspension was stirred for 18 h under hydrogen atmosphere. The reaction was filtered through a filter aide and the filtrate was concentrated in vacuo to give a residue (0.12 g, 66%) which was purified by chromatography (silica, 10% ethyl acetate in hexane). The oil was converted to the fumaric acid salt and crystallized from methanol/ether to give a solid (0.10 g): mp 150-152° C.; MS (ES) m/z 248 (M+); 1H NMR (DMSO-d6) 8.38 (1H, s), 8.24 (1H, d, J=0.8 Hz), 7.89 (1H, d, J=9.2 Hz), 7.70 (1H, d, J=9.2 Hz), 6.46 (2H, s), 4.44 (2H, m), 4.39 (2H, dd, J=6.8 Hz), 3.60 (1H, m), 1.36 (3H, t, J=7.2 Hz), 1.11 (3H, d, J=6.4 Hz). Analysis. Calculated for C13H17N3O2.C4H4O4.0.5H2O: C, 54.83; H, 5.95; N, 11.28. Found: C, 54.77; H, 5.95; N, 11.46.

Workup

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

Sources & evidence

ORD record
ord-e601f9fb32e44fea9dd451f27fa19cbe
Source dataset
uspto-grants-2008_10
Patent number
US07439262B1

Reaction notes

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