Acetic Acid → HCID 22238162, compound

HRID 2117348Notes

Reaction equation

HRID 2117348 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[C:11]([F:21])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[NH:24][C:25](=[O:42])[C:26]1[CH:31]=[C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)[CH:29]=[CH:28][C:27]=1[N+:39]([O-])=O.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Fe].O.C(O)C>[NH2:39][C:27]1[CH:28]=[CH:29][C:30]([N:32]2[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]2)=[CH:31][C:26]=1[C:25]([NH:24][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:2]=1[Cl:1])[C:6]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[C:11]([F:21])[CH:10]=1)=[O:7])=[O:42]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 22238147HCID 22238147, compound

Product 1

HCID 22238162HCID 22238162, compoundYield 53.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Iron powder (0.726 g) was added to a stirred suspension of 4-chloro-N-(3-fluoro-5-morpholinophenyl)-3-[5-(4-methylpiperazin-1-yl)-2-nitrobenzamido]benzamide (0.76 g), water (2 ml), acetic acid (0.5 ml) and ethanol (15 ml) and the resultant mixture was stirred and heated to reflux for 1 hour. The mixture was cooled to ambient temperature. Water (80 ml) was added and the mixture was basified by the addition of sodium carbonate. The resultant mixture was filtered through diatomaceous earth and the separated solids were washed in turn with methylene chloride and methanol. The combined filtrates were evaporated and the residue was triturated under ethyl acetate. The mixture was filtered and the filtrate was evaporated to give 3-[2-amino-5-(4-methylpiperazin-1-yl)benzamido]-4-chloro-N-(3-fluoro-5-morpholinophenyl)benzamide (0.385 g); Mass Spectrum: M+H+567.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. filtrationThe resultant mixture was filtered through diatomaceous earth
  4. washthe separated solids were washed in turn with methylene chloride and methanol
  5. customThe combined filtrates were evaporated
  6. customthe residue was triturated under ethyl acetate
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-3fdbb21a41964548b31f53944b6a7ed9
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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