Hydrochloric Acid → N-(1-(2-oxoethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide

HRID 624085

Reaktionsgleichung

C[O:2][CH:3](OC)[CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][O:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH:7]=[N:6]1.Cl.C([O-])(O)=O.[Na+]>C1COCC1>[O:2]=[CH:3][CH2:4][N:5]1[CH:9]=[C:8]([NH:10][C:11]([C:13]2[N:14]=[CH:15][O:16][C:17]=2[C:18]2[CH:19]=[C:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[O:12])[CH:7]=[N:6]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To N-(1-(2,2-dimethoxyethyl)-1H-pyrazol-4-yl)-5-(m-tolyl)oxazole-4-carboxamide (800 mg, 2.25 mmol) in THF (11.5 mL), 2 N aq. HCl-solution (10.3 mL, 20.60 mmol) was added dropwise and the resulting solution was refluxed (80° C.) for 1.5 h. The reaction mixture was allowed to reach rt, then neutralized with sat. aq. NaHCO3-solution and the org. solvent was removed under reduced pressure. The remaining aq. layer was extracted with EtOAc (2×) and the combined org. layer were washed with brine, dried (MgSO4), filtered and concentrated to obtain the title compound as a yellow solid which was used immediately in the next step. LC-MS conditions C: tR=0.72 min, [M+H2O+H]+=329.09.

Aufarbeitung

customto reach rt
customsolvent was removed under reduced pressure
extractionThe remaining aq. layer was extracted with EtOAc (2×)
washlayer were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-c22a4353ed574bde9b528ce25ba8b965
Quelldatensatz: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09303023B2

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