Hydrazine → 2-[2-Hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid hydrazide

HRID 470349Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:28]=[CH:27][C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([C:18]4[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:15]=[CH:14][C:13]=3[OH:26])[NH:11][C:7]=2[CH:6]=1)=O.[NH2:29][NH2:30]>CCO>[OH:26][C:13]1[CH:14]=[CH:15][C:16]([C:18]2[C:19]([O:24][CH3:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:17][C:12]=1[C:10]1[NH:11][C:7]2[CH:6]=[C:5]([C:3]([NH:29][NH2:30])=[O:2])[CH:28]=[CH:27][C:8]=2[N:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methyl ester (37.5 mg, 0.1 mmol) in EtOH (1 mL) was added anhydrous hydrazine (32 mg, 1 mmol). The reaction mixture was heated at 90° C. for 18 h, cooled to the room temperature, filtered to get the solid precipitate that was dried under reduced pressure to afford the title compound (25 mg, 33%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.51 (br s, 2H, NH), 7.11-7.17 (2H), 7.63 (d, J=9 Hz, 1H), 7.71 (d, J=9 Hz, 1H), 7.79-7.85 (2H), 8.10-8.21 (2H), 8.29 (s, 1H), 9.87 (br, 1H, NH). ESI-MS m/z 376.3 (MH+).

Workup

temperaturecooled to the room temperature
filtrationfiltered
customto get the solid precipitate that
customwas dried under reduced pressure

Sources & evidence

ORD record: ord-f3b1533297f24060ac710b4296653077
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629147B2

Reaction notes

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