Pyridine → HCID 178490841, compound

HRID 1175801Notes

Reaction equation

HRID 1175801 reaction equation
[NH2:1][C:2]1[N:3]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[N:4]=[C:5]2[C:14]3[C:13]([O:15]C)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][C:9]=3[N:8]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:7](=[O:28])[C:6]=12.[Br-].[Mg+2].[Br-].N1C=CC=CC=1>O>[NH2:1][C:2]1[N:3]([C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:31][CH:30]=2)[N:4]=[C:5]2[C:14]3[C:13]([OH:15])=[CH:12][C:11]([O:17][CH3:18])=[CH:10][C:9]=3[N:8]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[C:7](=[O:28])[C:6]=12

Participants

5

Reactant 3

HCID 1049PyridineHCID 82241Magnesium BromideHCID 23154068HCID 23154068, compound

Product 1

HCID 178490841HCID 178490841, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-amino-7,9-dimethoxy-5-(4-methoxybenzyl)-2-(4-phenoxyphenyl)-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (500 mg), magnesium bromide (168 mg) and pyridine (10 ml) was heated under reflux for 2 days, added water thereto after cooling. The precipitated solid was collected by filtration, washed with water, and purified with silica gel column chromatography to obtain the target compound (360 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. temperatureafter cooling
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. custompurified with silica gel column chromatography

Sources & evidence

ORD record
ord-7fde43a7f34249c982990118e8cf3a77
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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