Hydroxylamine → 1-[4-(4-[5-{2-(N-Hydroxyethanimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

HRID 1469223Notes

Reaction equation

HRID 1469223 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[O:14][N:13]=[C:12]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:38])[CH2:27][N:28]4[C:32]([CH3:33])=[CH:31][C:30]([C:34]([F:37])([F:36])[F:35])=[N:29]4)[CH2:22][CH2:21]3)[S:18][CH:19]=2)[CH2:11]1)(=O)[CH3:2].[NH2:39][OH:40].O>C(O)C>[OH:40][N:39]=[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[O:14][N:13]=[C:12]([C:15]2[N:16]=[C:17]([CH:20]3[CH2:21][CH2:22][N:23]([C:26](=[O:38])[CH2:27][N:28]4[C:32]([CH3:33])=[CH:31][C:30]([C:34]([F:36])([F:37])[F:35])=[N:29]4)[CH2:24][CH2:25]3)[S:18][CH:19]=2)[CH2:11]1)[CH3:2]

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 66584949HCID 66584949, compound

Product 1

HCID 764610551-[4-(4-[5-{2-(N-Hydroxyethanimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(4-{4-[5-(2-acetylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (150 mg) in ethanol (5 ml) was added dropwise hydroxylamine (50% in water, 4 eq.) at room temperature. After stirring at room temperature overnight, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave 1-[4-(4-{5-[2-(N-hydroxyethanimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone (33 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-ac636d88d2cf40bca1febae01db0df64
Source dataset
uspto-grants-2015_04
Patent number
US09006266B2

Reaction notes

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