Pyridine → HCID 23371739, compound

HRID 1899993Notes

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-0a4ed51d679d4b94b3ef91c0ea8d6f8e
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574042

Reaction notes

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