Hydroxyamine hydrochloride → 5-(4-Chloro-phenyl)-6-(4-isoxazol-5-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

HRID 1693510Notes

Reaction equation

HRID 1693510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([C:30](=[O:36])[CH:31]=[CH:32][N:33](C)C)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.NO.Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([C:30]3[O:36][N:33]=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 672827725-(4-Chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 116483975-(4-Chloro-phenyl)-6-(4-isoxazol-5-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a slurry of 5-(4-chloro-phenyl)-6-[4-(3-dimethylamino-acryloyl)-phenyl]-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one (8.0 mg, 0.016 mmol) in MeOH (0.5 mL) is added NH2OH.HCl (1.5 mg, 0.022 mmol). The mixture is heated to 80° C. for 2 h and cooled down to room temperature. After concentration under vacuum, the residue is purified by preparative LC/MS to provide the titled compound 5-(4-Chloro-phenyl)-6-(4-isoxazol-5-yl-phenyl)-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one as white solid.

Workup

  1. temperaturecooled down to room temperature
  2. concentrationAfter concentration under vacuum
  3. customthe residue is purified by preparative LC/MS

Sources & evidence

ORD record
ord-ee41eb5bdf62400f86d545af406de1e1
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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