HCID 178507511, compound → HCID 135461191, compound

HRID 2369822Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[NH:15][N:14]=[C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[CH:12]=1)=O>C(O)(=O)C>[NH:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:11]1[CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)[NH:14][N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Glacial acetic acid (1.0 mL) was added to a sealed tube charged with a solution of N-(2-aminophenyl)-3-[(E)-2-(4-hydroxyphenyl)ethenyl]-1H-pyrazole-5-carboxamide (0.044 g, 1.36 mmol) in xylenes (1.0 mL) and heated to 100° C. After twelve hours the reaction was cooled to room temperature and concentrated in vacuo. The residue was purified on reverse phase HPLC using water-acetonitrile gradient (0.1% TFA) to provide the title benzimidazole (10 mg, 25% yield) as a white solid: 1H NMR (400 MHz, CD3OD): δ 7.59 (bs, 2H), 7.41 (m, 2H), 7.25 (m, 2H), 7.16 (d, J=16.4 Hz, 1H), 7.03 (s, 1H), 6.92 (d, J=16.4 Hz, 1H), 6.79 (m, 2H); MS (EI) for C18H14N4O: 303.1 (MH+).

Workup

temperatureAfter twelve hours the reaction was cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified on reverse phase

Sources & evidence

ORD record: ord-df1c0efaecdc44ac84b3960e97a8e1da
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710038B2

Reaction notes

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