Pyridine → HCID 18923456, compound

HRID 1899996Notes

Reaction equation

Cl.Cl.[NH2:3][C:4]1[C:5]([Cl:24])=[C:6]([C:20]([Cl:23])=[CH:21][CH:22]=1)[CH2:7][O:8][C:9]1[C:10]2[N:11]([C:15]([Br:19])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1.N1C=CC=CC=1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32]>CN1CCCC1=O>[Br:19][C:15]1[N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:7][C:6]3[C:20]([Cl:23])=[CH:21][CH:22]=[C:4]([NH:3][C:34]([NH:33][CH2:31][CH3:32])=[O:35])[C:5]=3[Cl:24])[C:10]2=[N:17][C:16]=1[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of 8-(3-amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride (100 mg), pyridine (0.5 ml) and N-methylpyrrolidone (1.5 ml) was added ethyl isocyanate (0.10 ml). The mixture was stirred at 60° C. for 6 hours. The insoluble material was filtered off and washed with water. The filtrate and washings were combined and separated precipitate was collected by filtration. The precipitate was purified by preparative thin-layer chromatography (20% solution of methanol in dichloromethane) followed by recrystallization from n-hexane to give 3-bromo-8-[2,6-dichloro-3-(N'-ethylureido)benzyloxy]-2-methylimidazo[1,2-a]pyridine (13 mg) as crystals.

Workup

filtrationThe insoluble material was filtered off
washwashed with water
customseparated precipitate
filtrationwas collected by filtration
customThe precipitate was purified by preparative thin-layer chromatography (20% solution of methanol in dichloromethane)
customfollowed by recrystallization from n-hexane

Sources & evidence

ORD record: ord-268ea1620fda4c50856d050a3e4c628d
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574042

Reaction notes

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