Potassium Carbonate → HCID 117778208, compound

HRID 1500502Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH2:19].C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[CH3:14][O:15][C:16]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:17]=1[CH2:18][NH:19][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of methyl 6-chloro-4-methoxypyridine-3-carboxylate (1.09 g) in N,N-dimethylacetamide (12 mL), 2,4-dimethoxybenzylamine (1.35 g) and potassium carbonate (2.24 g) were added at room temperature, and the mixture was stirred at 120° C. for 19 hours. The reaction solution was cooled to room temperature, then diluted with ethyl acetate, and washed with water and saturated saline. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate) to obtain the title compound (1.16 g).

Workup

temperatureThe reaction solution was cooled to room temperature
washwashed with water and saturated saline
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-c36e2607e99a4896bc529f3385c934c8
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206168B2

Reaction notes

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