Hydrogen Peroxide → 2-(Ethylamino)-4-(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolin-1-yl)benzamide

HRID 1403076Notes

Reaction equation

HRID 1403076 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N:12]3[CH:16]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[N:14]=[CH:13]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:26]=1[NH:40][CH2:41][CH3:42])#[N:24].C(=O)([O-])[O-:44].[Na+].[Na+].[OH-].[Na+].OO>COCCOC.CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH2:41]([NH:40][C:26]1[CH:27]=[C:28]([C:2]2[C:11]3[C:6](=[C:7]([N:12]4[CH:16]=[C:15]([C:17]5[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=5)[N:14]=[CH:13]4)[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:29]=[CH:30][C:25]=1[C:23]([NH2:24])=[O:44])[CH3:42]

Participants

11

Reactant 5

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 898866621-Chloro-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolineHCID 1300535754-Cyano-3-(ethylamino)phenylboronic acid pinacol ester

Product 1

HCID 575206832-(Ethylamino)-4-(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolin-1-yl)benzamideYield 45%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Pd(PPh3)4 (0.012 g) was added to a solution of compound (1d) (0.062 g), 4-cyano-3-(ethylamino)phenylboronic acid pinacol ester (0.071 g), and an aqueous sodium carbonate solution (2 M, 1.5 mL) in ethylene glycol dimethyl ether (3.0 mL) in a nitrogen atmosphere, and the mixture was stirred at 85° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was used in the next reaction. An aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 30% aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained residue in DMSO (3 mL) and ethanol (1.5 mL) at room temperature, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, and the deposit was collected by filtration, then washed with water and ether by sprinkling, and then dried under reduced pressure to obtain compound (1) (0.040 g, yield based on 2 steps: 45%) as a pale yellow solid.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe obtained residue was used in the next reaction
  6. filtrationthe deposit was collected by filtration
  7. washwashed with water and ether by sprinkling
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-c6a3ffe0dba54245a36755dcd89f9bad
Source dataset
uspto-grants-2014_12
Patent number
US08912181B2

Reaction notes

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