Methanol → HCID 59725913, compound
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]=[C:14]([C:19]#N)[C:13]=3[N:12]=[CH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[O:21]1CCOC[CH2:22]1.Cl.C[OH:29]>>[CH3:22][O:21][C:19]([C:14]1[C:13]2[N:12]=[CH:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[C:18]=2[CH:17]=[CH:16][N:15]=1)=[O:29]Participants
Procedure
In 10 mL of methanol, 74 mg (0.28 mmol) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile prepared in Step A was dissolved, and 2 mL of a 4N hydrogen chloride dioxane solution was added thereto, and the mixture solution was refluxed under heating with stirring for four hours. The solvent was distilled under reduced pressure, 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 solvent was distilled and the residue was separated by Megabond Elute Silica Gel (2 g, dichloromethane:methanol=30:1) to obtain 34 mg (41%) of 1-(4-nitrophenyl)-1H-imidazo[4,5-c]pyridine-4-carboxylic acid methyl ester as a white solid.
Workup
- temperaturethe mixture solution was refluxed
- temperatureunder heating
- distillationThe solvent was distilled under reduced pressure
- 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
- distillationThe solvent was distilled
- customthe residue was separated by Megabond
- washElute Silica Gel (2 g, dichloromethane:methanol=30:1)
Sources & evidence
- ORD record
- ord-b3c2dd74925f4ea68f707a5b25bf2841
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609656B2
Reaction notes
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