Peracetic Acid → HCID 86627981, compound

HRID 910627Notes

Reaction equation

HRID 910627 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:38])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:37])[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]([CH3:35])[CH3:34])[C:26]3=[O:36])=[CH:21][CH:20]=2)=[N:6][CH:7]=1.C(OO)(=[O:41])C.C(=O)([O-])O.[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:38])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:11]=2[NH:17][C:18](=[O:37])[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]([CH3:35])([CH3:34])[O-:41])[C:26]3=[O:36])=[CH:21][CH:20]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6585Peracetic AcidHCID 516892Sodium BicarbonateHCID 16666750HCID 16666750, compound

Product 1

HCID 86627981HCID 86627981, compound

Reagents, catalysts & solvents 1

HCID 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. temperaturewith cooling with ice
  2. temperaturewith cooling with ice for 30 minutes
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c8a2f270347f445ba210d810b3ca84c5
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

Loading…