HCID 53812896, compound → HCID 53843236, compound

HRID 1004293Notes

Reaction equation

HRID 1004293 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]=[C:6]([C:23]1[CH:24]=[N:25][C:26]([NH2:29])=[CH:27][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH:6]([C:23]1[CH:24]=[N:25][C:26]([NH2:29])=[CH:27][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[CH2:19][CH2:18][CH2:17][NH:16][C:15]=2[N:14]=1)[CH3:2]

Participants

4

Reactant 1

HCID 53812896HCID 53812896, compound

Product 1

HCID 53843236HCID 53843236, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 28-5 (0.1 g, 0.3 mmol) and 10% Pd/C (0.1 g) in 10 mL methanol was purged with argon under vacuum and then treated under balloon hydrogenation conditions for 40 hr. It was filtered through a pad of celite. The solution was concentrated. The residue was purified by silica gel chromatography (100% CHCl3 to CHCl3 /MeOH 5:1) to afford the desired product 28-6 as an oil.

Workup

  1. customwas purged with argon under vacuum
  2. additiontreated under balloon hydrogenation conditions for 40 hr
  3. filtrationIt was filtered through a pad of celite
  4. concentrationThe solution was concentrated
  5. customThe residue was purified by silica gel chromatography (100% CHCl3 to CHCl3 /MeOH 5:1)

Sources & evidence

ORD record
ord-27b302404b324fabbc1da6b0d4f84454
Source dataset
uspto-grants-2000_04
Patent number
US06048861

Reaction notes

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