Water → (E)-N'-hydroxy-3-[4-[(E)-1-[1-(oxan-2-yl)indazol-5-yl]-2-phenylbut-1-enyl]phenyl]prop-2-enimidamide
Reaction equation
[C:1]1(/[C:7](/[CH2:34][CH3:35])=[C:8](\[C:24]2[CH:29]=[CH:28][C:27](/[CH:30]=[CH:31]/[C:32]#[N:33])=[CH:26][CH:25]=2)/[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20]O2)[N:13]=[CH:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:37][OH:38].C(N(CC)CC)C.[OH2:46]>CS(C)=O>[OH:38]/[N:37]=[C:32](\[NH2:33])/[CH:31]=[CH:30]/[C:27]1[CH:28]=[CH:29][C:24](/[C:8](/[C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:46]2)[N:13]=[CH:12]3)=[C:7](\[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)/[CH2:34][CH3:35])=[CH:25][CH:26]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a solution of (E)-3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylonitrile (380 mg, 0.83 mmol) and hydroxylamine hydrochloride (265 mg, 3.8 mmol) in DMSO (8 mL) was added triethylamine (0.5 mL, 3.8 mmol), and the mixture was heated at 75° C. for 24 h. After cooling, water was added, and the solution was extracted with EtOAc (3×). The combined organics were washed with brine (2×), dried (MgSO4) and concentrated. Purification by silica gel chromatography (0 to 65% EtOAc/hexanes) provided 116 mg of the title compound as a yellow foam. LCMS: 409 [(M-THP+H)+H]+.
Workup
- temperatureAfter cooling
- extractionthe solution was extracted with EtOAc (3×)
- washThe combined organics were washed with brine (2×)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customPurification by silica gel chromatography (0 to 65% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-8cd3b84ac3f2429fba9eab5a277b9de7
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399646B2
Reaction notes
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