Benzoic Acid → HCID 67391550, compound

HRID 910628Notes

Reaction equation

HRID 910628 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:38])[C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][N+:33](C)([CH3:35])[O-])[C:26]3=[O:37])=[CH:21][CH:20]=2)=[N:6][CH:7]=1.O.C(O)(=O)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>CN(C)C=O.[Fe](Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:38])[C:19]2[CH:24]=[CH:23][C:22]([CH:25]3[CH2:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][NH:33][CH3:35])[C:26]3=[O:37])=[CH:21][CH:20]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 86627981HCID 86627981, compound

Product 1

HCID 67391550HCID 67391550, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

N-(5-chloropyridin-2-yl)-2-[(4-{1-[2-(dimethylamino)ethyl]-2-oxopiperidin-3-yl}benzoyl)amino]-3-hydroxybenzamide (300 mg) was dissolved in dimethylformamide (6 mL), and with cooling with ice, an aqueous 32% peracetic acid solution (135 μL) was added, followed by stirring with cooling with ice for 30 minutes. The reaction solution was put into an aqueous saturated sodium hydrogencarbonate solution (30 ml), followed by extraction with chloroform. The organic layer was dried with sodium sulfate and evaporated under reduced pressure to obtain N-(5-chloropyridin-2-yl)-2-[(4-{1-[2-(dimethylnitroryl)ethyl]-2-oxopiperidin-3-yl}benzoyl)amino]-3-hydroxybenzamide (210 mg). The resulting N-(5-chloropyridin-2-yl)-2-[(4-{1-[2-(dimethylnitroryl)ethyl]-2-oxopiperidin-3-yl}benzoyl)amino]-3-hydroxybenzamide (209 mg) was dissolved in dimethylformamide (3 mL), then at room temperature, water (3 ml), benzoic acid (46 mg) and an aqueous 1 M iron chloride solution (38 μL) were added, followed by stirring at room temperature for 2 hours. An aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with chloroform. The organic layer was evaporated under reduced pressure, and the residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0 to 95:5). The purified product was dissolved in ethanol, and 4 M hydrochloric acid/ethyl acetate solution (1 mL) was added, followed by evaporation under reduced pressure. Ethyl acetate was added to the residue, followed by stirring at room temperature for 1 hour. The precipitate formed was collected by filtration and dried at 40° C. under reduced pressure to obtain N-(5-chloropyridin-2-yl)-3-hydroxy-2-[(4-{1-[2-(methylamino)ethyl]-2-oxopiperidin-3-yl}benzoyl)amino]benzamide hydrochloride (108 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. customThe organic layer was evaporated under reduced pressure
  3. customthe residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0 to 95:5)
  4. dissolutionThe purified product was dissolved in ethanol
  5. addition4 M hydrochloric acid/ethyl acetate solution (1 mL) was added
  6. customfollowed by evaporation under reduced pressure
  7. additionEthyl acetate was added to the residue
  8. stirringby stirring at room temperature for 1 hour
  9. customThe precipitate formed
  10. filtrationwas collected by filtration
  11. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-339609e178084b4c934c2a0bf7c791ba
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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