HCID 22285487, compound → HCID 22285397, compound

HRID 1062454Notes

Reaction equation

HRID 1062454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=2)[C:10]([CH3:22])=[C:11]([C:13]([NH:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])[N:12]=1>C(O)C.[Pd]>[NH2:29][C:26]1[CH:25]=[CH:24][C:23]([N:9]2[C:10]([CH3:22])=[C:11]([C:13]([NH:15][N:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:14])[N:12]=[C:8]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 22285487HCID 22285487, compound

Product 1

HCID 22285397HCID 22285397, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A sample of 2-(2-chlorophenyl)-5-methyl-1-(4-nitrophenyl)-N-(1-piperidinyl)-1H-imidazole-4-carboxamide (Table entry 41) (111 mg, 0.25 mmol) was added as a suspension in ethanol (5 mL) to Degussa-type palladium on carbon (10% by weight, 12 mg). The mixture was hydrogenated at atmospheric pressure and rt for 2 h. Filtration of the mixture through Celite and concentration of the filtrate gave 1-(4-aminophenyl)-2-(2-chlorophenyl)-5-methyl-N-(1-piperidinyl)-1H-imidazole-4-carboxamide as a yellow foam (104 mg, 100%). This material was used without purification for the preparation of compounds of the invention, such as Example 46.

Workup

  1. filtrationFiltration of the mixture through Celite and concentration of the filtrate

Sources & evidence

ORD record
ord-537b8e26ce034eec8b74ad001fa2f10d
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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