Ethylenediamine → 2-Amino-6-methoxypyridine

2-Chloro-6-methoxypyridine (5.0 g) was heated with ethylenediamine (30 ml) at 120° C. overnight. The excess ethylenediamine was removed by rotary evaporation. The residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide and extracted thoroughly with dichloromethane. The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo to give (2-aminoethyl)(6-methoxy(2-pyridyl)amine as an orange syrup. The amine (2.58 g) was treated with benzotriazole carboxamidinium 4-methylbenzenesulfonate (0.86 g) and DIEA (0.45 mmol) in acetonitrile (6 ml) and stirred overnight at room temperature. Trituration with ether gave the guanidine, amino-{2-[(6-methoxy(2-pyridyl))amino]ethyl}carboxamidinium 4-methylbenzenesulfonate, as an oil. The oily guanidine (200 mg) was reacted with 100 mg of resin according to Resin Method C (90° C., overnight) to give the title compound.

1. customThe excess ethylenediamine was removed by rotary evaporation
2. dissolutionThe residue was dissolved in a small volume of 2.5 M aqueous sodium hydroxide
3. extractionextracted thoroughly with dichloromethane
4. washThe combined organic layers were washed with saturated aqueous sodium chloride
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo

ORDレコード

ord-ddf58bae5335442a801057f4d75d7568

出典データセット

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07045519B2