HCID 9911005, compound → HCID 22707383, compound

HRID 993163Notes

Reaction equation

HRID 993163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][N:18]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=2)=[O:22])[CH2:17][CH2:16]1.[H][H]>C(O)C.O.[C].[Pd]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:21]([N:18]2[CH2:17][CH2:16][N:15]([C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][N:7]=3)[CH2:20][CH2:19]2)=[O:22])=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 9911005HCID 9911005, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22707383HCID 22707383, compoundYield 29%

Reagents, catalysts & solvents 3

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

Procedure

In 50 ml of ethanol was suspended 1.5 g (3.7 mmol) of 4-(6,7-dimethoxy-4-quinazolinyl)-N-(4-nitrophenyl)-1-piperazinecarboxamide obtained in Example 77, and a suspension of 500 mg of 10% palladium-carbon in 10 ml of water and 10 ml of ethanol was added thereto, followed by stirring in a stream of hydrogen at room temperature for 5 hours. After the catalyst was separated by filtration using Celite, the solvent was evaporated. Then, the residue was purified by silica gel chromatography and recrystallized from ethyl acetate to give the desired compound as colorless crystals.

Workup

  1. additionwas added
  2. customAfter the catalyst was separated by filtration
  3. customthe solvent was evaporated
  4. customThen, the residue was purified by silica gel chromatography
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c182d4691f314229a2d486caf304c594
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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