HCID 22010785, compound → HCID 22010879, compound

HRID 323164Notes

Reaction equation

HRID 323164 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:16]([NH:18][C:19]3[CH:51]=[CH:50][C:22]([C:23]([N:25]([CH3:49])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([N:42]5[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]5)=[O:41])=[CH:36][N:35]=4)=[O:24])=[CH:21][CH:20]=3)=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:16]([NH:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([N:25]([CH3:49])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]([N:42]5[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]5)=[O:41])=[CH:36][N:35]=4)=[O:24])=[CH:50][CH:51]=3)=[O:17])=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 22010785HCID 22010785, compound

Product 1

HCID 22010879HCID 22010879, compoundYield 54.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 4-(4′-nitrobiphenyl-2-carboxamido)-N-methyl-N-[2-[5-(4-methylpiperazin-1-ylcarbonyl)pyrid-2-ylmethoxy]phenyl]benzamide (300 mg) and iron powder (122 mg) in a mixture of ethanol (10 ml) and acetic acid (1 ml) was refluxed for 3 hours and the mixture was evaporated in vacuo. The residue was stirred in a mixture of chloroform (20 ml) and saturated aqueous sodium hydrogen carbonate (20 ml) at ambient temperature for 30 minutes and the mixture was filtered through a bed of Celite. The organic phase of the filtrate was separated and washed with brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give a syrup. The crude product was purified by silica gel column (chloroform:methanol:conc. ammonia=10:1:0.1) to give 4-(4′-aminobiphenyl-2-carboxamido)-N-methyl-N-[2-[5-(4-methylpiperazin-1-ylcarbonyl)pyrid-2-ylmethoxy]phenyl]benzamide (157 mg) as a pale yellow amorphous.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customthe mixture was evaporated in vacuo
  3. filtrationthe mixture was filtered through a bed of Celite
  4. customThe organic phase of the filtrate was separated
  5. washwashed with brine
  6. dry with materialThe organic solution was dried over magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customto give a syrup
  9. customThe crude product was purified by silica gel column (chloroform:methanol:conc. ammonia=10:1:0.1)

Sources & evidence

ORD record
ord-1bce2a8f033c46588372a3a9654c47f7
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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