Oxalic Acid → (E)-2-(3-Methyl-1-butenyl)-5-methoxy-1-(2-pyridyl)-1H-benzimidazole oxalate

HRID 50944Notes

Reaction equation

HRID 50944 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[C:5]([NH2:16])[CH:4]=1.[CH3:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21](Cl)=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50]>C(OCC)(=O)C>[C:48]([OH:53])(=[O:52])[C:49]([OH:51])=[O:50].[CH3:17][CH:18]([CH3:24])/[CH:19]=[CH:20]/[C:21]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:6]2[CH:14]=[CH:15][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[N:16]=1

Participants

6

Reactant 4

HCID 971Oxalic AcidHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 10986269(E)-4-methylpent-2-enoyl ChlorideHCID 227366532-amino-4-methoxy-N-(2-pyridyl)aniline

Product 1

HCID 22736729(E)-2-(3-Methyl-1-butenyl)-5-methoxy-1-(2-pyridyl)-1H-benzimidazole oxalate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Free base of the titled compound was prepared from 4-methoxy-2-amino-N-(2-pyridyl)aniline and (E)-4-methyl-2-pentenoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base and oxalic acid were dissolved into ethyl acetate. Concentration and recrystallization from ethyl acetate/n-hexane yielded the titled compound. MW: 383.41; mp: 140.0-141.0° C.; 1H-NMR (DMSO) δ: 8.71 (1H, d, J=3.7 Hz), 8.16-8.10 (1H, m), 7.64-7.56 (2H, m), 7.28 (1H, d, J=9.2 Hz), 7.19 (1H, d, J=2.2 Hz), 6.99-6.83 (2H, m), 6.37 (1H, d, J=15.8 Hz), 3.80 (3H, s), 2.52-2.42 (1H, m), 1.02 (6H, d, J=6.6 Hz).

Workup

  1. concentrationConcentration and recrystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-f7878a3faae84470af870e0fa80f3a47
Source dataset
uspto-grants-2004_03
Patent number
US06713482B2

Reaction notes

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