1,2-Ethanediamine, N1,N1,N2-trimethyl- → 2-Dimethylaminoethyl-4-(5-benzoylbenzimidazol-2-yl)-3,5-dimethylpyrrole-2-carboxamide

HRID 553239Notes

Reaction equation

Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[C:24]([C:32]1[CH:50]=[CH:49][C:35]2[N:36]=[C:37]([C:39]3[C:40]([CH3:48])=[C:41]([C:45]([OH:47])=O)[NH:42][C:43]=3[CH3:44])[NH:38][C:34]=2[CH:33]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH3:51][N:52]([CH3:57])[CH2:53][CH2:54][NH:55]C>N1C=CC=CC=1>[CH3:51][N:52]([CH3:57])[CH2:53][CH2:54][NH:55][C:45]([C:41]1[NH:42][C:43]([CH3:44])=[C:39]([C:37]2[NH:38][C:34]3[CH:33]=[C:32]([C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:50]=[CH:49][C:35]=3[N:36]=2)[C:40]=1[CH3:48])=[O:47]

Participants

Conditions

Temperature: 60 °C

Procedure

1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (88 mg, 0.46 mmol) and 1-hydroxybenzotriazole monohydrate (70 mg, 0.46 mmol) were added to a pyridine (2 ml) solution of the 4-(5-benzoylbenzimidazol-2-yl)-3,5-dimethylpyrrole-2-carboxylic acid (150 mg, 0.42 mmol) obtained in Example 10. N,N,N′-Trimethyl ethylenediamine (43 mg, 0.42 mmol) was added to the resultant solution and heated. The reaction mixture was stirred for 5 hours at 60° C. (internal temperature), and then allowed to cool to room temperature. The solvent was evaporated, and the residue was purified using medium pressure silica gel flash column chromatography (NH silica gel, chloroform:methanol=98:2) to afford N-methyl-N-(2-dimethylaminoethyl-4-(5-benzoylbenzimidazol-2-yl)-3,5-dimethylpyrrole-2-carboxamide (112 mg, 61%) as a light yellow amorphous.

Workup

temperatureheated
temperatureto cool to room temperature
customThe solvent was evaporated
customthe residue was purified

Sources & evidence

ORD record: ord-a5268f66b61e479eb4d13e383496dbbb
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951956B2

Reaction notes

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