HCID 86691849, compound → HCID 86691850, compound

HRID 1616235Notes

Reaction equation

HRID 1616235 reaction equation
[N:1]([C:4]([C:7]1[CH:8]=[CH:9][C:10]([CH3:29])=[C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH3:28])[C:20](=[O:27])[N:21]([CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[C:16]3=[CH:15][CH:14]=2)[CH:12]=1)([CH3:6])[CH3:5])=[N+]=[N-]>CCO.[Pd]>[NH2:1][C:4]([C:7]1[CH:8]=[CH:9][C:10]([CH3:29])=[C:11]([C:13]2[N:18]=[C:17]3[N:19]([CH3:28])[C:20](=[O:27])[N:21]([CH2:22][C:23]([CH3:25])([CH3:24])[CH3:26])[C:16]3=[CH:15][CH:14]=2)[CH:12]=1)([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 86691849HCID 86691849, compound

Product 1

HCID 86691850HCID 86691850, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 42-1 (1.4 g, 3.6 mmol) in EtOH (9 mL) was added 10% Pd/C (500 mg) and the flask was purged with hydrogen and fitted with a balloon filled with hydrogen gas. After 15 hours, the solution was filtered, concentrated and purified by reverse phase chromatography (1-100% Acetonitrile, 0.1% TFA in H2O) and the desired fractions were concentrated to give product. MS (M+H)+: observed=367.2, calculated=367.5.

Workup

  1. customthe flask was purged with hydrogen
  2. customfitted with a balloon
  3. additionfilled with hydrogen gas
  4. filtrationthe solution was filtered
  5. concentrationconcentrated
  6. custompurified by reverse phase chromatography (1-100% Acetonitrile, 0.1% TFA in H2O)
  7. concentrationthe desired fractions were concentrated
  8. customto give product

Sources & evidence

ORD record
ord-2c89460c218d49b3ad78b9e6ab285246
Source dataset
uspto-grants-2014_07
Patent number
US08765784B2

Reaction notes

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