HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chloro-6-methylaniline → 2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chloro-6-methylaniline | HCID 6897 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-(6-Bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid | HCID 49821884 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-(6-bromo-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-formamide | HCID 86676430 | 71.1% |
Reaction Steps
2-(6-bromo-2-methylpyrimidin-4-ylamino)thiazole-5-formic acid (Compound 12) (31.5 g, 0.1 mol), DMF (630 mL) and 2-chloro-6-methylaniline (Compound 8) (17.0 g, 0.12 mol) were mixed in a reaction flask, and then HATU (45.6 g, 0.2 mol) and triethylamine (25.3 g, 0.25 mol) was added when controlling the temperature at 20° C. Then the mixture reacted by stirring at room temperature overnight. After that water (3150 mL) was added and stirred for 30 min and then filtrated. The cake was dried to give target Compound 14 (31.2 g, yield: 71.1%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09108954B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-9313a04956d04866ad8bb5169078f8f7 |
| Source note | uspto-grants-2015_08 |