Hydroxyamine hydrochloride → 3-[2-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]-N'-hydroxy-2-oxo-1,3-benzoxazole-6-carboximidamide

HRID 1710651Notes

Reaction equation

HRID 1710651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:28])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]#[N:26])=[CH:24][C:19]=4[O:18][C:17]3=[O:27])[CH2:10][CH2:9]2)=[CH:4][C:3]=1[O:29][CH3:30].[NH2:31][OH:32].Cl>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:28])[CH2:15][N:16]3[C:20]4[CH:21]=[CH:22][C:23]([C:25]([NH:31][OH:32])=[NH:26])=[CH:24][C:19]=4[O:18][C:17]3=[O:27])[CH2:12][CH2:13]2)=[CH:4][C:3]=1[O:29][CH3:30]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 588343553-{2-[4-(4-Chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazole-6-carbonitrile

Product 1

HCID 1784930233-[2-[4-(4-chloro-3-methoxyphenyl)piperazin-1-yl]-2-oxoethyl]-N'-hydroxy-2-oxo-1,3-benzoxazole-6-carboximidamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-2-oxo-2,3-dihydro-benzooxazole-6-carbonitrile (49) (150 mg, 0.35 mmol, 1 eq), NH2OH.HCl (73 mg, 1.05 mmol, 3 eq), TEA (270 ml), in ethanol (2 ml) was stirred at 60° C. overnight. The resultant mixture was cooled and precipitated material was removed by filtration. The reaction solution was washed with ethyl acetate to provide 3-{2-[4-(4-chloro-3-methoxy-phenyl)-piperazin-1-yl]-2-oxo-ethyl}-N-hydroxy-2-oxo-2,3-dihydro-benzooxazole-6-carboxamidine (50).

Workup

  1. customprecipitated material
  2. customwas removed by filtration
  3. washThe reaction solution was washed with ethyl acetate

Sources & evidence

ORD record
ord-3ef9433646a54ba4a726f643bc2de6f1
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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