HuagongsheHuagongshe Chemistry Print Report · For research reference only
Heptane → 2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Heptane | HCID 8900 | — |
| Reactant | 4-Amino-2-methylpyridine | HCID 728670 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | 2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester | HCID 68406187 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide | HCID 11638418 | 41% |
Reaction Steps
A solution of 2-methyl-pyridin-4-ylamine (0.10 g, 0.91 mmol) in dry dioxane (2.00 ml) was added to a 2N solution of trimethylaluminium in heptane (0.46 ml, 0.91 mmol). The mixture was stirred at room temperature for 1 h, then 2-methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester (0.08 g, 0.30 mmol) was added and the reaction mixture was irradiated in a microwave oven at 150° C. for 15 min. The mixture was quenched with water (1.00 ml) and diluted with dichloromethane. After drying with sodium sulphate, the solvent was evaporated. The residue was purified by flash chromatography (dichloromethane/methanol) yielding the title compound (0.04 g, 41%) as a yellow solid, MS (ISP): m/e=326.1 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07678815B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-1e9ff39e875b4362a4b5fa5cfca656e8 |
| Source note | uspto-grants-2010_03 |