Sodium Carbonate → HCID 117667339, compound

HRID 1526183Notes

Reaction equation

HRID 1526183 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:15][C:16]2[C:17]([C:32]([NH2:34])=[O:33])=[N:18][CH:19]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=3)[N:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.[CH3:35][N:36]1[CH2:40][CH2:39][CH2:38][C:37]1=O.N1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH3:14][N:11]1[CH2:12][CH2:13][N:8]([C:7]2[CH:6]=[CH:5][C:4]([NH:15][C:16]3[C:17]([C:32]([NH2:34])=[O:33])=[N:18][CH:19]=[C:20]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=4)[N:21]=3)=[CH:3][C:2]=2[C:39]2[CH:40]=[CH:35][N:36]=[CH:37][CH:38]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 2734379(Pyridin-4-yl)boronic acidHCID 89709221HCID 89709221, compound

Product 1

HCID 117667339HCID 117667339, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 3-{[3-bromo-4-(4-methylpiperazin-1-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (500 mg), and N-methylpyrrolidone (5 mL) were added pyridin-4-ylboronic acid (407 mg), tetrakistriphenylphosphine palladium (0) (164 mg), and a 2 M aqueous sodium carbonate solution (2.84 mL), followed by stirring in a microwave reaction device at 140° C. for 1 hour. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-15:1:0.1) to obtain 3-{[4-(4-methylpiperazin-1-yl)-3-(pyridin-4-yl)phenyl]amino}-5-(3-nitrophenoxy)pyrazine-2-carboxamide (64 mg) as a yellow solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform:methanol:28% aqueous ammonia=1:0:0-15:1:0.1)

Sources & evidence

ORD record
ord-4824b05065bf46e0bfdfa188ad291a84
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

Loading…