Ethanol → N-{3-[6-(3-Amino-4-methylamino-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-4-tert-butyl-benzamide

HRID 551860Notes

Reaction equation

HRID 551860 reaction equation
[C:1]([C:5]1[CH:40]=[CH:39][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3[N:19]=[C:20]([NH:26][C:27]4[CH:32]=[CH:31][C:30]([NH:33][CH3:34])=[C:29]([N+:35]([O-])=O)[CH:28]=4)[C:21](=[O:25])[N:22]([CH3:24])[CH:23]=3)[C:13]=2[CH3:38])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.[H][H]>[Pd].C(OCC)(=O)C>[NH2:35][C:29]1[CH:28]=[C:27]([NH:26][C:20]2[C:21](=[O:25])[N:22]([CH3:24])[CH:23]=[C:18]([C:14]3[C:13]([CH3:38])=[C:12]([NH:11][C:9](=[O:10])[C:8]4[CH:39]=[CH:40][C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])=[CH:6][CH:7]=4)[CH:17]=[CH:16][CH:15]=3)[N:19]=2)[CH:32]=[CH:31][C:30]=1[NH:33][CH3:34]

Participants

6

Reactant 3

HCID 702EthanolHCID 587290344-tert-Butyl-N-{2-methyl-3-[4-methyl-6-(4-methylamino-3-nitro-phenylamino)-5-oxo-4,5-dihydro-pyrazin-2-yl]-phenyl}-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 58729140N-{3-[6-(3-Amino-4-methylamino-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-4-tert-butyl-benzamideYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-tert-butyl-N-{2-methyl-3-[4-methyl-6-(4-methylamino-3-nitro-phenylamino)-5-oxo-4,5-dihydro-pyrazin-2-yl]-phenyl}-benzamide (3) (500 mg), 10% palladium-on-carbon (100 mg), ethanol (50 mL), and ethyl acetate (100 mL) was hydrogenated at room temperature and 40 psi hydrogen for 16 hr. The mixture was filtered through a celite pad, washing with ethyl acetate (2×100 mL). The combined filtrates were evaporated to give N-{3-[6-(3-amino-4-methylamino-phenylamino)-4-methyl-5-oxo-4,5-dihydro-pyrazin-2-yl]-2-methyl-phenyl}-4-tert-butyl-benzamide (4) as a yellow solid (402 mg), m/z 512.08 (MH+).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered through a celite pad
  3. washwashing with ethyl acetate (2×100 mL)
  4. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-ab717b5518364ef68be5e2a036aa780f
Source dataset
uspto-grants-2011_05
Patent number
US07947835B2

Reaction notes

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