HCID 10480667, compound → 571141-49-6

HRID 1179459Notes

Reaction equation

HRID 1179459 reaction equation
[CH3:1][O:2][CH:3]([O:33][CH3:34])[C@@:4]1([CH3:32])[C@H:9]([OH:10])[C@@H:8]([N:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:12][C:13]2[NH:14][CH:15]=[CH:16][N:17]=2)[C:7]2[CH:25]=[C:26]([N+:29]([O-])=O)[CH:27]=[CH:28][C:6]=2[O:5]1>CO.[Pd]>[NH2:29][C:26]1[CH:27]=[CH:28][C:6]2[O:5][C@:4]([CH:3]([O:33][CH3:34])[O:2][CH3:1])([CH3:32])[C@H:9]([OH:10])[C@@H:8]([N:11]([C:18]3[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=3)[CH2:12][C:13]3[NH:14][CH:15]=[CH:16][N:17]=3)[C:7]=2[CH:25]=1

Participants

4

Reactant 1

HCID 10480667HCID 10480667, compound

Product 1

HCID 10434320571141-49-6Yield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the solution of the nitro compound (521 mg, 1.07 mmol) prepared from example 3 in methanol (3 mL) was added 10% Pd/C. The mixture was hydrogenated at room temperature under 3 atmosphere pressure of H2 for 12 hours, and filtered through a pad of Celite. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (5% methanol in dichloromethane) to afford the title compound (368 mg, 75%).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d3992f989568450b8ec6ba8b2dba3be9
Source dataset
uspto-grants-2007_10
Patent number
US07279497B2

Reaction notes

Loading…