HCID 57449634, compound → HCID 57449635, compound

HRID 907515Notes

Reaction equation

HRID 907515 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[CH2:8]>C(O)C.[Pd]>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:8]

Participants

4

Reactant 1

HCID 57449634HCID 57449634, compound

Product 1

HCID 57449635HCID 57449635, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Crude (13) in ethanol was hydrogenated (50 psi H2) over Pd/C (10%, 0.19 g) over night. The reaction was filtered through a bed of Celite. The filtrate was added silica gel, and the solvent was removed under vacuum. Crude product on silica was purified by chromatography on silica gel with 2% saturated ammonia methanol in dichloromethane to give (14) as a light tan foam (423 mg, 1.79 mmol, 73% over 2 steps).

Workup

  1. filtrationThe reaction was filtered through a bed of Celite
  2. additionThe filtrate was added silica gel
  3. customthe solvent was removed under vacuum
  4. customCrude product on silica was purified by chromatography on silica gel with 2% saturated ammonia methanol in dichloromethane

Sources & evidence

ORD record
ord-ce5217677dd242ae97402810406ef0c1
Source dataset
uspto-grants-2011_09
Patent number
US08013169B2

Reaction notes

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