Hydrochloric Acid → 4-(4-Aminofuro[3,2-c]pyridin-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile

HRID 1910667Notes

Reaction equation

[C:1]([C:3]1[CH:8]([C:9]2[O:17][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([NH:18]C(=O)C4C=CC=CC=4)[C:11]=3[CH:10]=2)[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]=1[CH3:30])#[N:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[NH2:18][C:12]1[C:11]2[CH:10]=[C:9]([CH:8]3[C:7]([C:27]#[N:28])=[C:6]([CH3:29])[NH:5][C:4]([CH3:30])=[C:3]3[C:1]#[N:2])[O:17][C:16]=2[CH:15]=[CH:14][N:13]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 43 mg (0.11 mmol) N-[2-(3,5-dicyano-2,6-dimethyl-1,4-dihydropyridin-4-yl)furo[3,2-c]pyridin-4-yl]benzamide (Example 4) in acetic acid (3 ml) was treated with 0.2 ml hydrochloric acid (37%) and stirred for 24 h at 100° C. Then, further 0.2 ml hydrochloric acid (37%) were added, and stirring was continued for 48 h at 100° C. Upon cooling, saturated aq. sodium carbonate solution was added until a neutral pH was reached. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine and water, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v) to afford the title compound (5.6 mg, 18% of th.) as a white solid.

Workup

stirringstirring
waitwas continued for 48 h at 100° C
temperatureUpon cooling
extractionThe mixture was extracted with ethyl acetate
washthe organic layer was washed with brine and water
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by preparative thin layer chromatography (silica, eluent dichloromethane/methanol 10:1 v/v)

Sources & evidence

ORD record: ord-671a3c3159754a598f2e9892b1b64c49
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604028B2

Reaction notes

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