Water → 5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole

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Reaktionsgleichung

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH2:13])[C:7]([NH2:12])=[CH:8][C:9]=1[CH2:10][CH3:11])[CH3:2].[N+:14]([C:17]1[C:18]([CH:28]=O)=[N:19][N:20]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:21]=1)([O-:16])=[O:15].S(=O)(O)[O-].[Na+].O>CN(C)C=O>[CH2:1]([O:3][C:4]1[C:9]([CH2:10][CH3:11])=[CH:8][C:7]2[NH:12][C:28]([C:18]3[C:17]([N+:14]([O-:16])=[O:15])=[CH:21][N:20]([CH:22]4[CH2:27][CH2:26][CH2:25][CH2:24][O:23]4)[N:19]=3)=[N:13][C:6]=2[CH:5]=1)[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 4-ethoxy-5-ethyl-benzene-1,2-diamine [0.18 g, Reference Example 30(s)], 4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carbaldehyde [0.225 g, Reference Example 6(m)] and sodium bisulfite (0.12 g, 1.2 mmol) in dimethylformamide (10 mL) was heated at 120° C. for 1 hour. The mixture was cooled, water (100 mL) was added and the aqueous mixture was extracted with twice ethyl acetate (50 mL). The combined extracts were evaporated and the residue was chromatographed on silica gel (ethyl acetate with gradient of 20-0% heptane) to give 5-ethoxy-6-ethyl-2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1H-benzoimidazole (200 mg) as a solid. LC-MS (Method E) RT=2.85 minutes, 386 (M+H)+.

Aufarbeitung

temperatureThe mixture was cooled
extractionthe aqueous mixture was extracted with twice ethyl acetate (50 mL)
customThe combined extracts were evaporated
customthe residue was chromatographed on silica gel (ethyl acetate with gradient of 20-0% heptane)

Quellen und Nachweise

ORD-Eintrag: ord-00266d80e81040ba9252ea7903a2ab37
Quelldatensatz: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08288425B2

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