HCID 22707354, compound → HCID 22707458, compound

HRID 353144Notes

Reaction equation

HRID 353144 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([NH:20][C:21]4[CH:26]=[CH:25][C:24]([O:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)=[CH:23][CH:22]=4)=[O:19])[CH2:14][CH2:13]3)=[N:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:34]([O-])=O>C(O)(=O)C.[Zn]>[NH2:34][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[N:9]=[CH:8][N:7]=[C:6]2[N:12]1[CH2:17][CH2:16][N:15]([C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:25][CH:26]=2)=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 22707354HCID 22707354, compound

Product 1

HCID 22707458HCID 22707458, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 628.8 mg (1.25 mmol) of 4-(7-chloro-6-nitro-4-quinazolinyl)-N-(4-phenoxyphenyl)-1-piperazinecarboxamide obtained in Example 357 in 15 ml of acetic acid was added 407.9 mg (6.24 mmol) of zinc dust, followed by overnight stirring in an atmosphere of argon at room temperature. After the zinc dust was separated by filtration using Celite, the filtrate was washed with a chloroform-methanol mixture. After the solvent was evaporated with triethylamine, the residue was purified by silica gel chromatography to give the desired compound as colorless crystals.

Workup

  1. customAfter the zinc dust was separated by filtration
  2. washthe filtrate was washed with a chloroform-methanol mixture
  3. customAfter the solvent was evaporated with triethylamine
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a7ed8b6daa4f49a89949c474243a3156
Source dataset
uspto-grants-2004_06
Patent number
US06750218B2

Reaction notes

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