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

HRID 2182420Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 120 °C

Procedure

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)+. (b) 2-[4-nitro-1-(tetrahydropyran-2-yl)-1H-pyrazol-3-yl]-1,5,6,7-tetrahydro-1,3-diaza-s-indacene

Workup

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)

Sources & evidence

ORD record: ord-527252f2c25545fc9f466cafe4a1e05f
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897208B2

Reaction notes

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