HuagongsheHuagongshe Chemistry Print Report · For research reference only
Azane;hydrate → 3-[5-(2-Aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Azane;hydrate | HCID 12896473 | — |
| Reactant | tert-Butyl {4-[4-(3-bromophenyl)-2-ethyl-1,3-thiazol-5-yl]pyridin-2-yl}carbamate | HCID 22932827 | — |
| Reactant | HCID 178418260 | HCID 178418260 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-[5-(2-Aminopyridin-4-yl)-2-ethyl-1,3-thiazol-4-yl]benzonitrile | HCID 22932726 | 57% |
Reaction Conditions
| Temperature | 150 °C |
|---|
Reaction Steps
To a solution of 4-(3-bromophenyl)-5-[2-(tert-butoxycarbonylamino)-4-pyridyl]-2-ethyl-1,3-thiazole (0.5 g, 1.1 mmol) in N,N-dimethylformamide (10 mL) was added copper cyanide (0.25 g, 1.6 mmol), and the mixture was stirred for 20 hours at 150° C. under argon atmosphere. Into the reaction mixture was poured ammonia water, and the deposit was removed, then, extracted with ethyl acetate. The extracts were washed with water, then, dried and concentrated. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=4:1) to obtain a crystal. This crystal was washed with hexane-ethyl acetate to obtain a title compound (0.19 g, yield 57%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07495018B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-dfbbf98668a64539acd92b5e65e31a42 |
| Source note | uspto-grants-2009_02 |