Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Hydrochloride methanol | HCID 21893726 | — |
| Reactant | 2-Amino-5-chloronicotinamide | HCID 66876883 | — |
| Reactant | HCID 68661652 | HCID 68661652 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 68662290 | HCID 68662290 | 2.8% |
Reaction Steps
To a solution of 2-amino-5-chloronicotinamide (0.15 g) in 35 N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-1-chloro-4-(methylsulfonyl)benzene (0.30 g), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was quenched with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate100%→ethyl acetate:methanol=4:1) to give a yellow solid. The obtained solid was dissolved in methanol, and 2N hydrochloric acid-methanol solution (0.1 ml) was added. The solvent was concentrated under reduced pressure and the residue was crystallized from methanol-ethyl acetate to give the title compound (5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08470859B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-0c9784448a454408a50d245e2d834761 |
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| Source note | uspto-grants-2013_06 |
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