Dimethylcarbamoyl Chloride → HCID 23154955, compound

HRID 1912806Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N+:15]([O-])=[CH:14][C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C[Si]([C:24]#[N:25])(C)C.CN(C)C(Cl)=O>CN(C)C=O.O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH:17]=[CH:16][N:15]=[C:14]([C:24]#[N:25])[C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

In a mixed solvent of 1 mL of dimethylformamide and 2 mL of dioxane, 100 mg (0.39 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine 5-oxide prepared in Step A of Example 90 was dissolved, and 310 μL (0.78 mmol) of tri-methylsilylcyanide and 144 μL (0.78 mmol) of N,N-dimethylcarbamoyl chloride were added thereto and the mixture solution was stirred at 90° C. for 14 hours. The solvent was distilled, and the residue was partitioned between ethyl acetate (10 mL×2) and a sodium hydrogencarbonate aqueous solution (10 mL). The combined organic layers was washed with a saturated sodium chloride solution, dried on anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was triturated with ethyl acetate to obtain 78 mg (75%) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a pale yellow solid.

Workup

distillationThe solvent was distilled
customthe residue was partitioned between ethyl acetate (10 mL×2)
washThe combined organic layers was washed with a saturated sodium chloride solution
dry with materialdried on anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-812ea7f9d55444cfa57cb8e02c0070be
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08609656B2

Reaction notes

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