Pyridinium chloride → HCID 69270816, compound

HRID 751538Notes

Reaction equation

C[O:2][C:3]1[CH:4]=[C:5]([C:12]2[C:13](=[O:33])[NH:14][C:15](=[O:32])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH:18]=2)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1.Cl.N1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([C:12]2[C:13](=[O:33])[NH:14][C:15](=[O:32])[C:16]=2[C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]([CH:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]3)[CH:18]=2)[C:6]2[O:10][CH:9]=[CH:8][C:7]=2[CH:11]=1

Participants

Reactant 2

HCID 10176127Pyridinium chloride

HCID 69270197HCID 69270197, compound

Product 1

HCID 69270816HCID 69270816, compoundYield 82.9%

Conditions

Temperature: 190 °C

Procedure

Combine 3-(5-methoxybenzofur-7-yl)-4-[1-(piperidin-4-yl)-1H-indol-3-yl]pyrrole-2,5-dione (0.125 g, 0.24 mmol) and pyridine hydrochloride (2.2 g, 18-fold excess by weight) under nitrogen. Attach a heating mantle and heat to 190° C. for 45 min. Let cool to 20° C., then extract with ethyl acetate versus water. Wash with brine, dry organic layer over magnesium sulfate, filter and concentrate. Purification by column chromatography (5% methanol: dichloromethane) gives 0.085 g (70%) product. High Res. Mass Spec (m/z): Calcd 518.2080 found 518.2080.

Workup

temperatureLet cool to 20° C.
extractionextract with ethyl acetate versus water
washWash with brine, dry organic layer over magnesium sulfate
filtrationfilter
concentrationconcentrate
customPurification by column chromatography (5% methanol: dichloromethane)

Sources & evidence

ORD record: ord-d65608d0f4bf40ef8273cb6bb378c975
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405305B2

Reaction notes

Loading…