HCID 178440777, compound → HCID 178440776, compound

HRID 1595407Notes

Reaction equation

HRID 1595407 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:12][C:13]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[C:14]([C:16]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[O:17])[N:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.CO.[Ni]>[NH2:30][C:27]1[CH:26]=[CH:25][C:24]([C:13]2[NH:12][C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:10][CH:9]=3)=[N:15][C:14]=2[C:16]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:17])=[CH:29][CH:28]=1

Participants

5

Reactant 1

HCID 178440777HCID 178440777, compound

Product 1

HCID 178440776HCID 178440776, compoundYield 46.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-tert-Butylphenyl)-5-(4-nitrophenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide (16.3 g) was dissolved in a mixed solvent of dioxane and methanol and hydrogenated with Raney nickel. The catalyst was filtered off and the residue was concentrated and crystallized from ethyl acetate and isopropyl ether to give 5-(4-aminophenyl)-2-(4-tert-butylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide (7.13 g). 1.0 g therefrom was converted to hydrochloride to give 5-(4-aminophenyl)-2-(4-tert-butylphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide hydrochloride (0.48 g), melting point 270-272° C. (decomposition).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe residue was concentrated
  3. customcrystallized from ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-f37e2e48015f4e8cb47b64c904c93bd6
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

Loading…