HCID 11316908, compound → HCID 11223943, compound

HRID 993180Notes

Reaction equation

HRID 993180 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([NH:30][CH2:31][CH3:32])=[C:24]([N+:27]([O-])=O)[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH2:13][CH2:12]1)=[S:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.[Fe]>[NH2:27][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][C:23]=1[NH:30][CH2:31][CH3:32])[N:20]=[CH:19][N:18]=[C:17]2[N:14]1[CH2:15][CH2:16][N:11]([C:9](=[S:10])[NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 1

HCID 11316908HCID 11316908, compound

Product 1

HCID 11223943HCID 11223943, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 4.26 g (9.44 mmol) of N-benzyl-4-(7-ethylamino-6-nitro-4-quinazolinyl)-1-piperazinethiocarboxamide obtained in Example 361 in 100 ml of ethanol and 10 ml of water were added 4.26 g (76.3 mmol) of iron powder and 430 mg (1.59 mmol) of ferric chloride hexahydrate under ice-cooling, followed by heating under reflux in an atmosphere of argon for 4 hours. After the iron powder was separated by filtration using Celite, the solvent was evaporated, and the residue was purified by silica gel chromatography to give the desired compound as colorless crystals.

Workup

  1. temperaturecooling
  2. temperatureby heating
  3. temperatureunder reflux in an atmosphere of argon for 4 hours
  4. customAfter the iron powder was separated by filtration
  5. customthe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-53630b55ebe94351a72e07b5c94d677c
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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