Pyridine → HCID 23371739, compound

HRID 1290176Notes

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.CN1C[CH2:35][CH2:34][C:33]1=[O:37].C(Cl)(=O)CC>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:33](=[O:37])[CH2:34][CH3:35])[C:5]=3[Cl:24])[C:10]2=[N:17][C:16]=1[CH3:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of 8-(3-amino-2,6-dichlorobenzyloxy)-3-bromo-2-methylimidazo[1,2-a]pyridine dihydrochloride (200 mg), pyridine (1 ml) and N-methylpyrrolidone (3 ml) was added propionyl chloride (78 mg) and the mixture was stirred at 60° C. for 1 hour. To the cooled mixture was added water, and the precipitate was collected by filtration and dissolved in chloroform. This organic solution was washed with water and brine respectively, dried with magnesium sulfate and concentrated in vacuo. The residue was collected by filtration and washed with ethyl acetate to give 3-bromo-8-(2,6-dichloro-3-propionylaminobenzyloxy)-2-methylimidazo [1,2-a]pyridine (158 mg).

Workup

filtrationthe precipitate was collected by filtration
dissolutiondissolved in chloroform
washThis organic solution was washed with water and brine respectively
dry with materialdried with magnesium sulfate
concentrationconcentrated in vacuo
filtrationThe residue was collected by filtration
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-927638e0cea44e1b924c6307c20f32a2
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750699

Reaction notes

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