3-Acetylpyridine → 3-morpholin-4-ylsulfonyl-N-[(E)-1-pyridin-3-ylethylideneamino]benzamide

HRID 1777034

Reaktionsgleichung

[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:15][NH2:16])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=O)[CH3:27])[CH:21]=1>CO.C(O)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([S:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=2)[C:13]([NH:15]/[N:16]=[C:26](/[C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)\[CH3:27])=[O:14])(=[O:9])=[O:8])[CH2:3][CH2:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

3-(Morpholinosulfonyl)benzohydrazide (40 mg, 0.140 mmol) and 1-(pyridin-3-yl)ethanone (16.98 mg, 0.140 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum, and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) affording the title compound as a solid (15 mg). 1H NMR (400 MHz, CDCl3): δ 9.53 (bs, 1H), 8.87 (s, 1H), 8.59 (m, 1H), 8.39 (m, 1H), 8.17 (m, 1H), 7.98 (m, 1H), 7.89 (d, 1H, J=8.0 Hz), 7.67 (t, 1H, J=8.0 Hz), 7.32 (m, 1H), 3.70 (m, 4H), 3.00 (m, 4H), 2.39 (s, 3H). ESI-MS: 389.0 [M+H]+.

Aufarbeitung

customUpon completion of the reaction
temperaturefollowing cooling
customthe solvent was removed by vacuum
customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-c1d4bc17c54c4421bd6d12c5796781d6
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09266838B2

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