HCID 66681846, compound → HCID 66682835, compound

HRID 530306Notes

Reaction equation

HRID 530306 reaction equation
[CH:1]1([N:7]([CH3:24])[C:8]([N:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([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>[NH2:21][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)[CH3:24])=[O:9])[CH:14]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 1

HCID 66681846HCID 66681846, compound

Product 1

HCID 66682835HCID 66682835, compoundYield 100.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (0.122 g, 0.115 mmol) was added to a stirred solution of N-cyclohexyl-N-methyl-4-(3-nitrophenyl)-1H-imidazole-1-carboxamide (0.755 g, 2.299 mmol) in a mixture of ethyl acetate (46 mL) and methanol (46 mL) under an atmosphere of argon at room temperature. The mixture was then allowed to stir at room temperature under an atmosphere of hydrogen for 50 minutes. The mixture was filtered through celite and the pad was washed with methanol. The combined filtrate was evaporated to give a clear oil/foam (691 mg, 100%) that was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe pad was washed with methanol
  3. customThe combined filtrate was evaporated

Sources & evidence

ORD record
ord-0c1cffea9ae84bfab25a69f9d2f78a29
Source dataset
uspto-grants-2016_05
Patent number
US09353082B2

Reaction notes

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