Water → HCID 178484072, compound

HRID 491774Notes

Reaction equation

HRID 491774 reaction equation
[CH3:1][N:2]([CH3:34])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:24]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=2)=[O:25])=[O:10])[CH2:5][CH2:4]1.[Sn](Cl)Cl.O.[OH-].[Na+]>C(O)C.O1CCCC1>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]2[O:14][C:13]([C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][N:28]=3)=[O:25])=[C:12]([NH:11][C:9]([C@H:6]3[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[CH3:34])[CH2:4][CH2:5]3)=[O:10])[C:16]=2[CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 178484075HCID 178484075, compound

Product 1

HCID 178484072HCID 178484072, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-nitro-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (3.00 g) obtained in Example 18 is suspended in ethanol (100 ml), and thereto are added tin(II) chloride (anhydrous) (7.02 g) and water (1.0 ml). The mixture is heated under reflux for 7 hours, and allowed to stand for cooling. To the reaction solution are added 10% aqueous sodium hydroxide solution (30 ml) and tetrahydrofuran (200 ml), and the mixture is stirred at room temperature for one hour. The insoluble materials are filtered on celite, and the filtrate is concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then chloroform/ethyl acetate=1/1). The resulting residue is suspended in ethyl acetate/n-hexane, and the precipitates are collected by filtration and dried to give trans-5-amino-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide (1.43 g). This product (35 mg) is dissolved in ethanol, and treated with 4N hydrogen chloride/ethyl acetate to give the title compound (43 mg).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 7 hours
  3. temperaturefor cooling
  4. filtrationThe insoluble materials are filtered on celite
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. custompurified by silica gel column chromatography (eluent
  7. filtrationthe precipitates are collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-6d91ad21a3ca407d8c357bc8c4c1a558
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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