HCID 59184658, compound → HCID 59686846, compound

HRID 426131Notes

Reaction equation

HRID 426131 reaction equation
C([O:8][C:9]1[N:14]=[C:13]([C:15]([C:17]2[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=2)[C:20]#[N:21])=[O:16])[C:12]([C:26]([CH3:29])([CH3:28])[CH3:27])=[C:11]([O:30]CC2C=CC=CC=2)[N:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[C:26]([C:12]1[C:11](=[O:30])[NH:10][C:9](=[O:8])[NH:14][C:13]=1[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([CH3:25])[CH:24]=1)[C:20]#[N:21])=[O:16])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 59184658HCID 59184658, compound

Product 1

HCID 59686846HCID 59686846, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The solution of (57) (1.1 g, 2.237 mmol) in ethanol (20 ml) was stirred in the presence of 10% palladium on carbon under an atmosphere of hydrogen. After 1.5 hr., the mixture was filtered through celite pad and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, methanol:chloroform (5:95)) to afford 786 mg (quantitative) of the title compound as a white solid. m.p. 270-271° C.; 1H NMR (200 MHz, CDCl3) δ 1.00 (9H, s), 2.47 (3H, s), 7.70 (1H, s), 7.86 (1H, s), 8.02 (1H, s), 10.74 (1H, s), 11.01 (1H, s); m/z (EI) 311 (M+).

Workup

  1. filtration, the mixture was filtered through celite pad
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by silica gel column chromatography (eluent, methanol:chloroform (5:95))

Sources & evidence

ORD record
ord-5f545d8aa5254140abde6282b4b92322
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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