HCID 44513536, compound → HCID 59292873, compound

HRID 2409760Notes

Reaction equation

HRID 2409760 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([C:26]2[C:31]([Cl:32])=[C:30]([O:33][CH3:34])[CH:29]=[C:28]([O:35][CH3:36])[C:27]=2[Cl:37])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)=[O:15])C1C=CC=CC=1>CO.[Pd]>[NH:8]1[CH:12]=[CH:11][N:10]=[C:9]1[NH:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([C:26]2[C:31]([Cl:32])=[C:30]([O:33][CH3:34])[CH:29]=[C:28]([O:35][CH3:36])[C:27]=2[Cl:37])=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)=[O:15]

Participants

4

Reactant 1

HCID 44513536HCID 44513536, compound

Product 1

HCID 59292873HCID 59292873, compoundYield 2.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 5-(2,6-dichloro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid (1-benzyl-1H-imidazol-2-yl)-amide (Example 160) (100 mg, 1.16 mmol) and palladium hydroxyde (75 mg) in MeOH (5 mL) was stirred for 72 h at rt, under a hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 1:4) followed by trituration in Et2O to provide 15 mg of the title compound as a yellow solid: ES-MS: 442.9 [M+H]+; tR=4.05 min (System 1); TLC: Rf=0.08 (Hex/EtOAc, 1:4).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 1:4)

Sources & evidence

ORD record
ord-a1fd0f54305d4aeb86661d6ff0fda39f
Source dataset
uspto-grants-2014_08
Patent number
US08815901B2

Reaction notes

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