Cesium carbonate → N-(3-(2-methyl-2H-pyrazol-3-yl)-4-(2-methyl-2-nitropropoxy)phenyl)acetamide

HRID 521638Notizen

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].CS([O:11][CH2:12][C:13]([CH3:18])([N+:15]([O-:17])=[O:16])[CH3:14])(=O)=O.O[C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:29])[CH3:28])=[CH:22][C:21]=1[C:30]1[N:31]([CH3:35])[N:32]=[CH:33][CH:34]=1>CC(N(C)C)=O>[CH3:35][N:31]1[C:30]([C:21]2[CH:22]=[C:23]([NH:26][C:27](=[O:29])[CH3:28])[CH:24]=[CH:25][C:20]=2[O:11][CH2:12][C:13]([CH3:18])([N+:15]([O-:17])=[O:16])[CH3:14])=[CH:34][CH:33]=[N:32]1

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

Cesium carbonate (7.04 g, 21.6 mmol) was added to a solution of 2-methyl-2-nitropropyl methanesulfonate (2.39 g, 12.1 mmol) and N-(4-hydroxy-3-(2-methyl-2H-pyrazol-3-yl)phenyl)acetamide (2.00 g, 8.65 mmol) in dimethylacetamide (15 mL) and the mixture was stirred at 160° C. After 2 h, the solvent was evaporated, and the residue was triturated with water. The precipitate was isolated by filtration, washed with water and dried in vacuo to afford the product (2.38 g, 83%) as a tan solid. LCMS m/z (%)=333.4 (M+H 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (s, 6H), 2.02 (s, 3H), 3.53 (s, 3H), 4.32 (s, 2H), 6.15 (d, J=2.02 Hz, 1H), 7.14 (d, J=8.84 Hz, 1H), 7.44 (d, J=1.77 Hz, 1H), 7.49 (d, J=2.78 Hz, 1H), 7.62 (dd, J=8.97, 2.65 Hz, 1H), 9.94 (s, 1H).

Aufarbeitung

customthe solvent was evaporated
customthe residue was triturated with water
customThe precipitate was isolated by filtration
washwashed with water
customdried in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-2fed6ae5df6a4a3295c3b54a530c61c1
Quelldatensatz: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09328107B2

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