Hydroxylamine HCl → 5-[(4Z)-4-amino-4-hydroxyiminobutyl]-N-cyclopropyl-1-[4-(ethylcarbamoyl)phenyl]triazole-4-carboxamide

HRID 1717418Notes

Reaction equation

HRID 1717418 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=2)[N:9]=[N:8][C:7]=1[C:22]([NH:24][CH:25]1[CH2:27][CH2:26]1)=[O:23])#[N:2].[Cl-].[OH:29][NH3+:30].C(=O)([O-])O.[Na+]>CS(C)=O.[Cl-].[Na+].O>[NH2:2]/[C:1](=[N:30]\[OH:29])/[CH2:3][CH2:4][CH2:5][C:6]1[N:10]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([NH:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:16]=2)[N:9]=[N:8][C:7]=1[C:22]([NH:24][CH:25]1[CH2:26][CH2:27]1)=[O:23]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 516892Sodium BicarbonateHCID 57665055HCID 57665055, compound

Product 1

HCID 576650325-[(4Z)-4-amino-4-hydroxyiminobutyl]-N-cyclopropyl-1-[4-(ethylcarbamoyl)phenyl]triazole-4-carboxamideYield 79%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 5-(3-cyanopropyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (366 mg, 1.0 mmol) obtained in Example 1207, hydroxyammonium chloride (139 mg, 2.0 mmol, 2.0 eq.) and sodium hydrogen carbonate (168 mg, 2.0 mmol, 2.0 eq.) in DMSO (5 ml) was stirred at 90° C. for 5 hr. Saturated brine (10 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (30 ml×3), and dried over anhydrous sodium sulfate. The solvent was evaporated and the residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1) to give the title compound as a colorless powder (315 mg, 79%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (30 ml×3)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column (hexane/ethyl acetate=1/1 to ethyl acetate/methanol=4/1)

Sources & evidence

ORD record
ord-464480ca23bd41ba83d3dadf7412360d
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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