M-Phenylenediamine → 5-[(3-Aminophenyl)amino]-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526205Notes

Reaction equation

HRID 1526205 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=1[CH2:8][CH3:9].[C:27]1([NH2:34])[CH:32]=[CH:31][CH:30]=[C:29]([NH2:33])[CH:28]=1>CN1CCCC1=O>[NH2:33][C:29]1[CH:28]=[C:27]([NH:34][C:2]2[N:3]=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[CH:16][CH:15]=3)[C:5]([C:10]([NH2:12])=[O:11])=[N:6][C:7]=2[CH2:8][CH3:9])[CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 885697045-Chloro-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide

Product 1

HCID 1176670445-[(3-Aminophenyl)amino]-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamideYield 50.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 5-chloro-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (200 mg), 1,3-phenylenediamine (288 mg), and N-methylpyrrolidone (0.8 mL) was reacted in a microwave device at 200° C. for 30 minutes. The mixture was subjected to liquid separation by the addition of ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution were added thereto for extraction. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-200:10:1), and was washed with ethyl acetate to obtain 5-[(3-aminophenyl)amino]-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (120 mg).

Workup

  1. customwas reacted in a microwave device at 200° C. for 30 minutes
  2. customThe mixture was subjected to liquid separation by the addition of ethyl acetate
  3. additiona saturated aqueous sodium hydrogen carbonate solution were added
  4. extractionfor extraction
  5. washThe organic phase was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-200:10:1)
  9. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-2e4a29de7fdc41a5817a2cfe7d12c6fc
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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