HCID 66688379, compound → 4-(3-Amino-4-methoxyphenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide

HRID 530311Notes

Reaction equation

HRID 530311 reaction equation
[CH:1]1([N:7]([CH3:26])[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([N+:23]([O-])=O)[CH:16]=3)[N:12]=[CH:11]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(OCC)(=O)C.CO>[NH2:23][C:17]1[CH:16]=[C:15]([C:13]2[N:12]=[CH:11][N:10]([C:8]([N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH3:26])=[O:9])[CH:14]=2)[CH:20]=[CH:19][C:18]=1[O:21][CH3:22]

Participants

5

Reactant 1

HCID 66688379HCID 66688379, compound

Product 1

HCID 666818744-(3-Amino-4-methoxyphenyl)-N-cyclohexyl-N-methyl-1H-imidazole-1-carboxamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (0.16 g, 0.15 mmol) was added to a stirred solution of N-cyclohexyl-4-(4-methoxy-3-nitrophenyl)-N-methyl-1H-imidazole-1-carboxamide (1.075 g, 3 mmol) in a mixture of ethyl acetate (50 mL) and methanol (50 mL) at room temperature under an argon atmosphere. Hydrogen was bubbled through the solution for 1 h. The solution was then filtered through celite and the pad was washed with ethyl acetate. The combined filtrate was evaporated to give a brown oily solid that was used in the next step without further purification.

Workup

  1. customHydrogen was bubbled through the solution for 1 h
  2. filtrationThe solution was then filtered through celite
  3. washthe pad was washed with ethyl acetate
  4. customThe combined filtrate was evaporated
  5. customto give a brown oily solid that
  6. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-9a525b4ee9f04d708b89de2c1eba71cc
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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