HCID 22707433, compound → HCID 22707738, compound

HRID 993166Notes

Reaction equation

HRID 993166 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:25][CH:24]=4)=[O:21])[CH2:16][CH2:15]3)=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.O.[C].[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8]([N:14]3[CH2:15][CH2:16][N:17]([C:20]([NH:22][C:23]4[CH:24]=[CH:25][C:26]([O:29][C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)=[CH:27][CH:28]=4)=[O:21])[CH2:18][CH2:19]3)=[N:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1

Participants

6

Reactant 2

HCID 22707433HCID 22707433, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22707738HCID 22707738, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 455.6 mg (0.97 mmol) of 4-(7-nitro-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide obtained in Example 322 in 10 ml of ethanol was added a suspension of 100 mg of 10% palladium-carbon in 5 ml of ethanol and 2 ml of water, followed by stirring in a stream of hydrogen at room temperature for 4 hours. After the catalyst was separated by filtration using Celite, the solvent was evaporated. The residue was purified by silica gel chromatography to give the desired compound as colorless crystals.

Workup

  1. customAfter the catalyst was separated by filtration
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ca5f70650244754aac4b935932657c4
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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