Potassium Carbonate → 5-(3-Bromo-5-nitrophenoxy)-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide

HRID 1526233Notes

Reaction equation

HRID 1526233 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].[Br:27][C:28]1[CH:29]=[C:30]([OH:37])[CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1.C(=O)([O-])[O-].[K+].[K+].CN1CCCC1=O>O>[Br:27][C:28]1[CH:29]=[C:30]([CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1)[O:37][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]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 104889843-Bromo-5-nitrophenolHCID 885697045-Chloro-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide

Product 1

HCID 1176670625-(3-Bromo-5-nitrophenoxy)-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamideYield 90.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (250 mg), 3-bromo-5-nitrophenol (170 mg), potassium carbonate (138 mg), and N-methylpyrrolidone (5 mL) was stirred at 100° C. for 4 hours. To the reactant was added water, followed by extraction with ethyl acetate. The organic phase was washed with water and 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=1:0-9:1) to obtain 5-(3-bromo-5-nitrophenoxy)-6-ethyl-3-{[4-(4-methylpiperazin-1-yl)phenyl]amino}pyrazine-2-carboxamide (336 mg) as a yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=1:0-9:1)

Sources & evidence

ORD record
ord-7825572cad8548bca0e5efb087d0906a
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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