6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole → 3-(6-Imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-4-iodo-1H-pyridin-2-one

HRID 1793698Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

The suspension of 6-imidazol-1-yl-2-(4-iodo-2-methoxy-pyridin-3-yl)-4-methyl-1H-benzimidazole in 1 N HCl (6 mL) was heated to 70° C. for 3 days, cooled to room temperature, and diluted with ethyl acetate. After extraction, the combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (1% NH4OH/10% MeOH/CH2Cl2) to yield the title compound (78 mg, 81%) as a solid. 1H NMR (300 MHz, CD3OD) δ 8.12 (1H, s), 7.58 (2H, s), 7.29–7.31 (2H, m), 7.16 (1H, s), 7.01 (1H, J=6.8 Hz), 2.66 (3H, s). LCMS (M+H)+ m/z 418 (t=0.75 min.)

Workup

temperaturecooled to room temperature
extractionAfter extraction
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residue was purified by flash chromatography (1% NH4OH/10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ab4500b11a8942d39110467a871b3764
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081454B2

Reaction notes

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