Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Bis(2-chloroethyl) ether | HCID 8115 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 21106440 | HCID 21106440 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 21106435 | HCID 21106435 | 59.8% |
Reaction Steps
To a solution of 100 mg of 1-(4-{4-[3-(4-Amino-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-yl}-2,6-dimethyl-piperazin-1-yl)-ethanone (0.246 mMol, 1.00 equiv) in 2 mL of DMF was added 100 μL of 2-chloroethyl ether, 50 mg of sodium iodide and 100 mg of K2CO3. After 3 hr at 110° C. the reaction was concentrated and purified by flash chromatography (EtOAc) to yield 70 mg of 1-(2,6-Dimethyl-4-{4-[3-(4-morpholin-4-yl-phenylamino)-[1,2,4]triazol-1-yl]-pyridin-2-yl}-piperazin-1-yl)-ethanone (0.147 mMol, 59.8% yield). 1H NMR (500 MHz, DMSO-d6) ∂ 9.26 (1H, s), 9.21 (1H, s), 8.20 (1H, d), 7.52 (2H, d), 7.21(1H, s), 7.12 (1H, d), 6.90 (2H, d), 4.30 (2H, m), 4.05 (2H, m), 3.73 (4H, m), 3.09 (2H, m), 2.99 (4H, m), 2.51 (3H, s), 1.2 (6H, m) ppm. LC/MS: 1.78 min/477.3 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07226920B2 |
|---|
| Source dataset | uspto-grants-2007_06 |
|---|
| ORD ID | ord-4bcb4b6ccd5d4efa821bc68f191139cb |
|---|
| Source note | uspto-grants-2007_06 |
|---|