Methyl dichloroacetate → 2-(Dichloromethyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine
Reaction equation
[NH2:1][N:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]1=[NH2+:12].CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[Cl:26][CH:27]([Cl:32])[C:28](OC)=O.C([O-])([O-])=O.[K+].[K+]>CCO>[Cl:26][CH:27]([Cl:32])[C:28]1[N:12]=[C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[N:8][C:9]=3[CH:10]=[CH:11][N:2]2[N:1]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 6-amino-1,6-naphthyridin-5(6H)-iminium-2,4,6-trimethylbenzenesulfonate (3.30 g, 9.17 mmol), methyl 2,2-dichloroacetate (3.93 g, 27.5 mmol) and K2CO3 (3.80 g, 27.5 mmol) in EtOH (30 mL) was refluxed for 14 h. The mixture was then cooled to room temperature, filtered, and washed with DCM (3×20 mL). The combined organic layers were concentrated under reduced pressure. The residue was dissolved in EtOAc (100 mL), washed with brine (5×10 mL), dried with Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography using DCM as eluent to yield 2-(dichloromethyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine as a white solid (500 mg, yield 29%). ESI MS: m/z 253, 255 [M+H]+.
Workup
- temperaturewas refluxed for 14 h
- filtrationfiltered
- washwashed with DCM (3×20 mL)
- concentrationThe combined organic layers were concentrated under reduced pressure
- dissolutionThe residue was dissolved in EtOAc (100 mL)
- washwashed with brine (5×10 mL)
- dry with materialdried with Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-3ac3314ed3d64ddcbfdc08e22489b4e7
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249162B2
Reaction notes
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