Hydrochloric Acid → HCID 22010673, compound

HRID 323162Notes

Reaction equation

HRID 323162 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[NH:35][C:36]([C:38]1[C:39]([C:44]2[CH:49]=[CH:48][C:47]([N+:50]([O-])=O)=[CH:46][CH:45]=2)=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:37])[C:6]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]1)=[O:24])[CH3:9])=[O:7].[H][H].[ClH:55]>CO.C(O)C.[OH-].[Pd+2].[OH-]>[ClH:55].[ClH:55].[NH2:50][C:47]1[CH:48]=[CH:49][C:44]([C:39]2[C:38]([C:36]([NH:35][C:34]3[CH:33]=[CH:32][C:5]([C:6]([N:8]([C:10]4[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=4[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[O:24])[CH3:9])=[O:7])=[CH:4][C:3]=3[O:2][CH3:1])=[O:37])=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:45][CH:46]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 22010578HCID 22010578, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22010673HCID 22010673, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of 3-methoxy-4-(4′-nitrobiphenyl-2-carboxamido)-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]-N-methylbenzamide (910 mg), 20% palladium hydroxide (200 mg) in methanol (30 ml) was stirred under atmospheric pressure of hydrogen at ambient temperature. After 5 hours, the reaction mixture was filtered through a bed of Celite, and the solvent was removed by evaporation and the crude product was purified by silica gel column chromatography (SiO2; 30 g, 5% methanol in chloroform) to give free product. To a solution of this product (810 mg) in ethanol (20 ml) was added 1N hydrochloric acid (2.39 ml) and stirred at ambient temperature for 10 minutes. The solvent was removed to give 4-(4′-aminobiphenyl-2-carboxamido)-3-methoxy-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]-N-methylbenzamide dihydrochloride as amorphous.

Workup

  1. filtrationthe reaction mixture was filtered through a bed of Celite
  2. customthe solvent was removed by evaporation
  3. customthe crude product was purified by silica gel column chromatography (SiO2; 30 g, 5% methanol in chloroform)
  4. customto give free product
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-c8b5070ba2e6491f806ad140eaddaba9
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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