Sodium Carbonate → 2-[5-(N-hydroxy-carbamimidoyl)-2-benzyloxy-phenyl]-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-acetamide acetate

HRID 31504Notes

Reaction equation

HRID 31504 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:7]([CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])=[C:15]([CH3:26])[CH:14]=2)=[O:11])[CH:8]=1)#[N:2].Cl.[NH2:36][OH:37].[C:38](=[O:41])([O-])[O-:39].[Cs+].[Cs+].[C:44](=O)([O-])[O-].[Na+].[Na+]>CO.O>[OH:37][NH:36][C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:7]([CH2:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])=[C:15]([CH3:26])[CH:14]=2)=[O:11])[CH:8]=1)=[NH:2].[C:38]([O-:39])(=[O:41])[CH3:44]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 10796Cesium carbonateHCID 443297Hydroxyamine hydrochlorideHCID 693109202-(5-cyano-2-benzyloxy-phenyl)-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-acetamide

Product 1

HCID 1784758712-[5-(N-hydroxy-carbamimidoyl)-2-benzyloxy-phenyl]-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-acetamide acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.1 g (2.5 mmol) of 2-(5-cyano-2-benzyloxy-phenyl)-N-[3-methyl-4-(pyrrolidin-1-yl-carbonyl)-phenyl]-acetamide are dissolved in 100 ml of methanol and combined with a solution of 300 mg (5 mmol) of hydroxylamine hydrochloride in 2.0 ml of water. After the addition of 800 mg (2.5 mmol) of caesium carbonate and 300 mg (3.0 mmol) of sodium carbonate the reaction mixture is refluxed for 6 hours. After cooling and the addition of 0.5 l of ice water the crude product obtained is suction filtered and purified on silica gel, eluting first with methylene chloride and methylene chloride/ethanol (19:1), then with methylene chloride/ethanol (9:1+1% glacial acetic acid and 4:1+1% glacial acetic acid). The uniform fractions are combined and concentrated by evaporation.

Workup

  1. temperatureis refluxed for 6 hours
  2. temperatureAfter cooling
  3. customobtained
  4. filtrationfiltered
  5. custompurified on silica gel
  6. washeluting first with methylene chloride and methylene chloride/ethanol (19:1)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f0b7c2cc59ce426f84494f0baa0d2f1c
Source dataset
uspto-grants-2008_09
Patent number
US07425641B2

Reaction notes

Loading…