Ethylenediamine → 6-(4,5-dihydro-1H-imidazol-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide hydrochloride

HRID 2363710Notes

Reaction equation

[ClH:1].[C:2]1([NH:8][C:9]([C:11]2[N:12]=[C:13]3[CH:18]=[CH:17][C:16]([C:19](=[NH:23])OCC)=[CH:15][N:14]3[CH:24]=2)=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25](N)[CH2:26][NH2:27]>C(O)C>[ClH:1].[NH:27]1[CH2:26][CH2:25][N:23]=[C:19]1[C:16]1[CH:17]=[CH:18][C:13]2[N:14]([CH:24]=[C:11]([C:9]([NH:8][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[N:12]=2)[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 296 mg of ethyl 2-phenylcarbamoylimidazo[1,2-a]pyridine-6-carboximidate hydrochloride (1:1) in 10 mL of ethanol is cooled to 0° C., followed by addition of 144 μL of ethylenediamine. The reaction mixture is refluxed for 16 hours and then stirred at room temperature for 60 hours. The precipitate is filtered off by suction and washed with ethanol and then recrystallized from methanol to give 64 mg of 6-(4,5-dihydro-1H-imidazol-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide hydrochloride (1:2) in the form of a white solid. The filtrate is concentrated to dryness and taken up in water. The insoluble matter is filtered off by suction, washed with methanol and then dried to give 99 mg of 6-(4,5-dihydro-1H-imidazol-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide hydrochloride (1:1) in the form of a white solid.

Workup

temperatureThe reaction mixture is refluxed for 16 hours
filtrationThe precipitate is filtered off by suction
washwashed with ethanol
customrecrystallized from methanol

Sources & evidence

ORD record: ord-3bc34e3d66a14c04be18efcb14e656a3
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691990B2

Reaction notes

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